Benzyl Bromide → HCID 19809150, compound

HRID 373981Notes

Reaction equation

HRID 373981 reaction equation
[OH:1][CH:2]([CH2:25][O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:3][N:4]([CH2:14][CH:15]([OH:24])[CH2:16][O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1.[CH2:33](Br)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.[OH-].[K+]>C(O)CC>[CH2:33]([O:13][C:10]1[CH:9]=[CH:8][C:7]([CH2:6][CH2:5][N:4]([CH2:14][CH:15]([OH:24])[CH2:16][O:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:3][CH:2]([OH:1])[CH2:25][O:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:12][CH:11]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 14797Potassium HydroxideHCID 19809105HCID 19809105, compound

Product 1

HCID 19809150HCID 19809150, compound

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

A solution of 1.0 g of p-[2-[bis[(RS)-2-hydroxy-3-phenoxypropyl]amino]ethyl]phenol, 0.27 ml of benzyl bromide and 257 mg of potassium hydroxide in 30 ml of n-propanol was heated to 120° for 18 hours. The reaction mixture was poured on to ice-water and extracted with ethyl acetate. The crude product obtained after evaporation of the solvent was chromatographed on silica gel. The fractions which were uniform according to thin-layer chromatography were recrystallized from acetone-hexane and yielded pure 1,1'-[[p-(benzyloxy)phenethyl]imino]bis-[(RS)-3-phenoxy-2-propanol], m.p. 106°-110°, ε219 =30020.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe crude product obtained
  3. customafter evaporation of the solvent
  4. customwas chromatographed on silica gel
  5. customwere recrystallized from acetone-hexane

Sources & evidence

ORD record
ord-b53071e00c384e4a8ea7092613f2a44b
Source dataset
uspto-grants-1992_11
Patent number
US05166218

Reaction notes

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