Benzyl Bromide → (S)-N-Benzyl-1(4-benzyloxyphenoxy)-3-[N-2-(4-hydroxyphenyl)ethylamino]propan-2-ol

HRID 1541

Reaction equation

HRID 1541 reaction equation
[CH2:1]([O:8][C:9]1[CH:29]=[CH:28][C:12]([O:13][CH2:14][C@@H:15]([OH:27])[CH2:16][NH:17][CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:30](Br)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[CH2:30]([N:17]([CH2:16][C@H:15]([OH:27])[CH2:14][O:13][C:12]1[CH:28]=[CH:29][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:10][CH:11]=1)[CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 10340Sodium CarbonateHCID 9908577(S)-1-(4-Benzyloxyphenoxy)-3-[N-2-(4-hydroxyphenyl)ethylamino]propan-2-ol

Product 1

HCID 22883068(S)-N-Benzyl-1(4-benzyloxyphenoxy)-3-[N-2-(4-hydroxyphenyl)ethylamino]propan-2-ol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (S)-1-(4-benzyloxyphenoxy)-3-[N-2-(4-hydroxyphenyl)ethylamino]propan-2-ol (1.9 g, 4.8 mMol) and benzyl bromide (0.57 ml, 4.8 mMol) in dimethylformamide (10 ml) containing sodium carbonate (770 mg, 7.2 mMol) was stirred at room temperature for 18 hours. The mixture was filtered and the residue was washed with ethyl acetate. The filtrates were combined, washed with water and brine, dried and evaporated. Purification of the residue by flash chromatography (silica gel, 50% ethyl acetate in hexane) gave the title compound.

Workup

  1. filtrationThe mixture was filtered
  2. washthe residue was washed with ethyl acetate
  3. washwashed with water and brine
  4. customdried
  5. customevaporated
  6. customPurification of the residue by flash chromatography (silica gel, 50% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-c88884b2244548bda021d31a20f133fd
Source dataset
uspto-grants-1998_03
Patent number
US05726165

Linked notes

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