Triethylamine → 7,8-Dimethoxy-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carbonyl chloride

HRID 657572Notes

Reaction equation

HRID 657572 reaction equation
O=C(Cl)[O:3][C:4]([Cl:7])(Cl)Cl.[CH3:9][O:10][C:11]1[C:21]([O:22][CH3:23])=[CH:20][C:14]2[CH2:15][CH2:16][NH:17][CH2:18][CH2:19][C:13]=2[CH:12]=1.C(N(CC)CC)C>ClCCl>[CH3:9][O:10][C:11]1[C:21]([O:22][CH3:23])=[CH:20][C:14]2[CH2:15][CH2:16][N:17]([C:4]([Cl:7])=[O:3])[CH2:18][CH2:19][C:13]=2[CH:12]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10426DiphosgeneHCID 129234297,8-Dimethoxy-2,3,4,5-tetrahydro-1H-3-benzazepine

Product 1

HCID 866286287,8-Dimethoxy-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carbonyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 1.2 mL (10 mmol/1 eq.) of diphosgene in 20 mL of dichloromethane, at about 0° C., there are added, dropwise, a solution of 3.55 g (20 mmol) of 7,8-dimethoxy-2,3,4,5-tetrahydro-1H-3-benzazepine in 22 mL of dichloromethane, and then 4.2 mL (30 mmol/1.5 eq.) of triethylamine. Stirring overnight at ambient temperature and then concentration are carried out. The residue is taken up in dichloromethane, washed with water and dried over magnesium sulphate to yield, after concentration, the desired product.

Workup

  1. concentrationconcentration
  2. washwashed with water
  3. dry with materialdried over magnesium sulphate
  4. customto yield
  5. concentrationafter concentration

Sources & evidence

ORD record
ord-e3fb737e68f447fc86c7a2affe197dae
Source dataset
uspto-grants-2011_12
Patent number
US08076325B2

Reaction notes

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