Water → 3-acetyl-2,3,4,5-tetrahydro-1H-3-benzazepine

HRID 33201Notes

Reaction equation

HRID 33201 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.[CH2:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[CH2:12][CH2:11][NH:10][CH2:9]1.C(N(CC)CC)C.O>ClCCl>[C:5]([N:10]1[CH2:9][CH2:8][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[CH2:12][CH2:11]1)(=[O:7])[CH3:6]

Participants

6

Reactant 4

HCID 962WaterHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 14002432,3,4,5-Tetrahydro-1H-benzo(d)azepine

Product 1

HCID 193754873-acetyl-2,3,4,5-tetrahydro-1H-3-benzazepineYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of acetic anhydride (6.37 g, 0.062 mol) in dichloromethane (50 ml) was added dropwise to a stirred solution of 2,3,4,5-tetrahydro-1H-3-benzazepine (8.35 g, 0.057 mol) and triethylamine (8.7 ml) in dichloromethane (50 ml) at 0° C. under argon. After stirring at room temperature for 18 h, water (80 ml) was added and the organic layer separated. The organic layer was washed with 0.5 M hydrochloric acid (50 ml), saturated sodium bicarbonate solution (50 ml), water (50 ml) and then dried (Na2SO4). Evaporation of the solvent in vacuo gave the title compound (10.24 g, 95%) as a yellow oil which solidified on standing.

Workup

  1. customthe organic layer separated
  2. washThe organic layer was washed with 0.5 M hydrochloric acid (50 ml), saturated sodium bicarbonate solution (50 ml), water (50 ml)
  3. dry with materialdried (Na2SO4)
  4. customEvaporation of the solvent in vacuo

Sources & evidence

ORD record
ord-7f2a0783a8a54f55a0f436fccf6024bc
Source dataset
uspto-grants-2008_09
Patent number
US07429579B2

Reaction notes

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