CHo — 



HO 



N-p-hydroxybenzylmorphol ine 

 "A 7~ CHj-N-CHj-CHj- 



OH 



HO 



N-p-hydroxybenzylaminoet'hanol 



.CH2-CH2-OH 

 'CH2-CH2-OH 



2,2'-(p-hydroxybenzylimino) diethanol 



o- 



N 



\, 



Fig. IV 



2^4 \c": 



,-CI + 2HN O 



\ / 



/ \ / \ / ^ 



■^OM-U >^-CH- - N + NH- 



\ / ^ \ / \ / 



If m.p. 79-79. 5°C 



■mJ/ >^-CH, - N O + 6(H) 1__ H,N-/ y-CH, — N 



Ml m.p. 99. 5-100. S°C 



0/ ^' / \ ' ' 



CH2 - N O+HjSO^+HNOj — ►HOjSONj-V y-CHj - N 



Fig. V 



Ij-V / '^^^2" \ O+HjO — HO-^ / ^"2" ^ 



/ \ 



O + Nj l-HjSO^ 



HO 



-/ \-C=0+H2N-CH2CH2-OH ► HO -^ Vc=N-CH2CH20H + H^ 



II m.p. 169-170°C 



HO 



^ \_C=N-CH2CH2-OH+ 2(H) L_^ HO V' V CH2-N-CH2CH2OH 



ANALYSIS 



Calc'd Found 

 II %N 8.49 8.19 

 IV %N 16.6 16.5 



HO 



-^ \- CH2-N-CH2CH2OH -O 



IV m.p. 203d 



HN — C=0 



I I 



C CH-NO, 



I I ' 



HN — C=0 



Fig. VI 



0- U 



