Triethylamine → HCID 12789222, compound

HRID 2286403Notes

Reaction equation

HRID 2286403 reaction equation
[CH3:1][O:2][C:3]1[C:13]([O:14][CH3:15])=[CH:12][C:6]2[CH2:7][CH2:8][NH:9][CH2:10][CH2:11][C:5]=2[CH:4]=1.C(N(CC)CC)C.Cl[C:24]([O:26][CH2:27][CH3:28])=[O:25]>C1(C)C=CC=CC=1>[C:24]([N:9]1[CH2:10][CH2:11][C:5]2[CH:4]=[C:3]([O:2][CH3:1])[C:13]([O:14][CH3:15])=[CH:12][C:6]=2[CH2:7][CH2:8]1)([O:26][CH2:27][CH3:28])=[O:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 129234297,8-Dimethoxy-2,3,4,5-tetrahydro-1H-3-benzazepine

Product 1

HCID 12789222HCID 12789222, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred solution of 42.6 g. (0.206 mole) of 7,8-dimethoxy-2,3,4,5-tetrahydro-1H-3-benzazepine in 1 l. of toluene were added 35.7 ml. of triethylamine (0.256 mole) and 24.5 ml. of ethyl chloroformate (0.256 mole), at room temperature, and the mixture was refluxed for 12 hours. The reaction mixture was filtered to remove triethylamine hydrochloride and the filtrate was concentrated. The solid residue (57 g.) was recrystallized from ethyl acetate to give 3-carboethoxy-7,8-dimethoxy-2,3,4,5-tetrahydro-1H-3-benzazepine, m.p. 91°-93° C.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove triethylamine hydrochloride
  3. concentrationthe filtrate was concentrated
  4. customThe solid residue (57 g.) was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-77c4119c820d49d499b1e84444b22ed0
Source dataset
uspto-grants-1981_05
Patent number
US04265890

Reaction notes

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