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

HRID 1668597Notes

Reaction equation

HRID 1668597 reaction equation
Cl.[CH2:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][CH2:5][NH:4][CH2:3]1.C(Cl)Cl.[C:16](OC(=O)C)(=[O:18])[CH3:17]>>[CH2:6]1[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[CH2:2][CH2:3][N:4]([C:16](=[O:18])[CH3:17])[CH2:5]1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 7918Acetic AnhydrideHCID 170652302,3,4,5-Tetrahydro-1H-3-benzazepine--hydrogen chloride (1/1)

Product 1

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

Procedure

To a solution of 2,3,4,5-Tetrahydro-1H-benzo[d]azepine hydrochloride (7.0 g) in DCM (200 ml) Et3N (12.1 ml, 2.5 eq) was added followed by a dropwise addition of acetic anhydride (4 ml). After 2 h the mixture was washed in sequence with 1N HCl, 5% aqueous NaHCO3 and brine, then dried over Na2SO4 and concentrated to afford a white solid (6.9 g, 95% yield).

Workup

  1. washAfter 2 h the mixture was washed in sequence with 1N HCl, 5% aqueous NaHCO3 and brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-20cf29048cb945a58091b8b55dbe7f48
Source dataset
uspto-grants-2011_08
Patent number
US07989444B2

Reaction notes

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