Triethylamine → 3-(2-Chloroethyl)-N-[3-(tert-butyldimethylsiloxy-methyl)benzyl]benzamide

HRID 1006069Notes

Reaction equation

HRID 1006069 reaction equation
[Cl:1][CH2:2][CH2:3][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7](Cl)=[O:8].[O:13]([CH2:21][C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=1)[CH2:25][NH2:26])[Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15].C(N(CC)CC)C>C(OCC)(=O)C>[Cl:1][CH2:2][CH2:3][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([NH:26][CH2:25][C:24]1[CH:27]=[CH:28][CH:29]=[C:22]([CH2:21][O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:15])[CH3:16])[CH:23]=1)=[O:8]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 220499793-(tert-Butyldimethylsiloxymethyl)benzylamineHCID 226753583-(2-Chloroethyl)benzoyl chloride

Product 1

HCID 226753683-(2-Chloroethyl)-N-[3-(tert-butyldimethylsiloxy-methyl)benzyl]benzamideYield 75%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent3×

Procedure

A solution of 3-(2-chloroethyl)benzoyl chloride (2.43 g, 12.0 mmol) in ethyl acetate (10 mL) was added to a solution of 3-(tert-butyldimethylsiloxymethyl)benzylamine (3.01 g, 12.0 mmol) and triethylamine (3.3 mL, 24 mmol) in ethyl acetate (20 mL) at 0° C., and the resulting mixture was stirred at the same temperature for 2 hours and then at room temperature for 3 hours. The reaction mixture was diluted with ethyl acetate, washed successively with a 5% aqueous potassium hydrogensulfate solution, water, a saturated aqueous sodium hydrogencarbonate solution and a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified by a silica gel column chromatography (silica gel 200 mL; hexane/ethyl acetate=10/1 to 3/1) to obtain the title compound (3.74 g, 75%) as a white solid.

Workup

  1. waitat room temperature for 3 hours
  2. washwashed successively with a 5% aqueous potassium hydrogensulfate solution, water
  3. dry with materiala saturated aqueous sodium hydrogencarbonate solution and a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by a silica gel column chromatography (silica gel 200 mL; hexane/ethyl acetate=10/1 to 3/1)

Sources & evidence

ORD record
ord-569b4340983b4f61bd43fecc721372ac
Source dataset
uspto-grants-2004_09
Patent number
US06787560B2

Reaction notes

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