Sodium Carbonate → Benzenemethanamine, 3-bromo-N-cyclopropyl-N,4-dimethyl-

HRID 1869939Notes

Reaction equation

HRID 1869939 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][C:14]=1[CH3:15])[C:5]([N:7]([CH:9]1[CH2:11][CH2:10]1)[CH3:8])=O.C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][C:14]=1[CH3:15])[CH2:5][N:7]([CH:9]1[CH2:10][CH2:11]1)[CH3:8]

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 211071533-Bromo-N-cyclopropyl-4,N-dimethyl-benzamide2×

Product 1

HCID 21107149Benzenemethanamine, 3-bromo-N-cyclopropyl-N,4-dimethyl-Yield 63.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-bromo-N-cyclopropyl-4,N-dimethyl-benzamide (Intermediate 96, 5.3 g, 19.77 mmol) in anhydrous tetrahydrofuran (50 mL) was treated with borane-methyl sulfide complex (10 mL, 100 mmol) and the resulting reaction mixture was refluxed for 2 h. It was cooled to ambient temperature and carefully treated with saturated, aqueous sodium carbonate solution till cessation of effervescence, and extracted with diethyl ether (×2). The combined organic phase was dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to an oil. Flash column chromatography over silica gel (230-400 mesh) using 10% ethyl acetate in hexane as the eluent afforded the title product as an oil (3.2 g, 63%).

Workup

  1. customthe resulting reaction mixture
  2. temperaturewas refluxed for 2 h
  3. extractionextracted with diethyl ether (×2)
  4. dry with materialThe combined organic phase was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo to an oil

Sources & evidence

ORD record
ord-92aef33835b642d4a31b14feb51fe19f
Source dataset
uspto-grants-2009_12
Patent number
US07638648B2

Reaction notes

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