Triethylamine → HCID 66878657, compound

HRID 1878427Notes

Reaction equation

HRID 1878427 reaction equation
[CH3:1][C@@H:2]([NH2:5])[CH2:3][CH3:4].C(N(CC)CC)C.[Cl:13][CH2:14][C:15]1[CH:16]=[C:17]([CH:21]=[CH:22][CH:23]=1)[C:18](Cl)=[O:19]>ClCCl>[C@H:2]([NH:5][C:18](=[O:19])[C:17]1[CH:21]=[CH:22][CH:23]=[C:15]([CH2:14][Cl:13])[CH:16]=1)([CH2:3][CH3:4])[CH3:1]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2724537(R)-sec-butylamineHCID 27333243-(Chloromethyl)benzoyl chloride

Product 1

HCID 66878657HCID 66878657, compoundYield 77.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of (R)-butan-2-amine (14.77 mmol, 1.478 mL, 1,081 g) and triethylamine (15.48 mmol, 2.157 mL, 1.566 g) in dichloromethane was added dropwise to a stirred solution of 3-(chloromethyl)benzoyl chloride (14.07 mmol, 2 mL, 2.66 g) in dichloromethane at room temperature. Upon complete addition the reaction was stirred for 2 hours, after which time the solvent was removed under vacuum and ethyl acetate (100 mL) added. The organic solution was then washed with water (200 mL), dried over sodium sulphate and concentrated under vacuum to give the title compound (2.47 g) as a cream solid. MS (ESI) m/z 226.3[M+H]+

Workup

  1. additionUpon complete addition the reaction
  2. customafter which time the solvent was removed under vacuum and ethyl acetate (100 mL)
  3. additionadded
  4. washThe organic solution was then washed with water (200 mL)
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-c9d1018363784583b93a90e2901195ad
Source dataset
uspto-grants-2012_11
Patent number
US08314091B2

Reaction notes

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