Benzyl Bromide → HCID 18427235, compound
Reaction equation
[NH2:1][CH:2]([CH2:5][OH:6])[CH2:3][OH:4].[H-].[Na+].[CH2:9](Br)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].[CH2:28](Br)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C1COCC1>[CH2:9]([O:4][CH2:3][CH:2]([NH2:1])[CH2:5][O:6][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 2-amino-1,3-propanediol in THF is added dropwise with vigorous stirring to a suspension of sodium hydride over a period of 45 minutes to 2 hrs. The reaction mixture is stirred at room temperature for an additional hr and sequentially treated with a solution of one equivalent each of octadecyl bromide and benzyl bromide, respectively. The reaction mixture is stirred at room temperature for 4-14 hrs. The reaction mixture is worked up by extraction with methylene chloride. The methylene chloride layer is washed with water (3×50 mL), saturated NaCl (1×50 mL) and dried (MgSO4). The dried organic layer is evaporated under vacuum to afford the product as a white solid.
Workup
- stirringThe reaction mixture is stirred at room temperature for 4-14 hrs
- extractionThe reaction mixture is worked up by extraction with methylene chloride
- washThe methylene chloride layer is washed with water (3×50 mL), saturated NaCl (1×50 mL)
- dry with materialdried (MgSO4)
- customThe dried organic layer is evaporated under vacuum
Sources & evidence
- ORD record
- ord-f012cdd77d3a4454b5da2b56b39c7d00
- Source dataset
- uspto-grants-2002_04
- Patent number
- US06379930B1
Reaction notes
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