Formaldehyde → trimopam

HRID 596630Notes

Reaction equation

HRID 596630 reaction equation
[CH3:1][O:2][C:3]1[C:19]([O:20][CH3:21])=[CH:18][C:6]2[CH:7]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH2:8][NH:9][CH2:10][CH2:11][C:5]=2[CH:4]=1.[CH2:22]=O>C(O)=O>[CH3:1][O:2][C:3]1[C:19]([O:20][CH3:21])=[CH:18][C:6]2[CH:7]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH2:8][N:9]([CH3:22])[CH2:10][CH2:11][C:5]=2[CH:4]=1

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 105409631H-3-Benzazepine, 2,3,4,5-tetrahydro-7,8-dimethoxy-1-phenyl-

Product 1

HCID 5024trimopam

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A solution of 3.58 g. (0.0126 mol) of 7,8-dimethoxy-1-phenyl-2,3,4,5-tetrahydro-1H-3 -benzazepine in 15 ml. of formic acid and 10 ml. of formaldehyde is refluxed for 18 hours. The reaction mixture is evaporated to dryness, 20 ml. of 6N hydrochloric acid is added and the solution is again evaporated to dryness to give a liquid. The latter is treated with 20 ml. of 10% sodium hydroxide solution and the mixture is extracted with ether. The dried extract is evaporated to give the liquid 7,8-dimethoxy-3-methyl-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine.

Workup

  1. customThe reaction mixture is evaporated to dryness, 20 ml
  2. additionof 6N hydrochloric acid is added
  3. customthe solution is again evaporated to dryness
  4. customto give a liquid
  5. additionThe latter is treated with 20 ml
  6. extractionof 10% sodium hydroxide solution and the mixture is extracted with ether
  7. extractionThe dried extract
  8. customis evaporated

Sources & evidence

ORD record
ord-3c311c32b51e48cd9d32d7f1330e5a30
Source dataset
uspto-grants-1977_03
Patent number
US04011319

Reaction notes

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