Formaldehyde → trimopam

HRID 972348Notes

Reaction equation

HRID 972348 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-97c0d6969e624b6d9ab17a7b0eca9b6c
Source dataset
uspto-grants-1977_10
Patent number
US04052506

Reaction notes

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