Formaldehyde → HCID 12928524, compound

HRID 894463Notes

Reaction equation

HRID 894463 reaction equation
[Cl:1][C:2]1[C:18]([O:19][CH3:20])=[CH:17][C:5]2[C@H:6]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH2:7][NH:8][CH2:9][CH2:10][C:4]=2[CH:3]=1.[CH2:21]=O>C(O)=O>[Cl:1][C:2]1[C:18]([O:19][CH3:20])=[CH:17][C:5]2[C@H:6]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH2:7][N:8]([CH3:21])[CH2:9][CH2:10][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 12928521HCID 12928521, compound

Product 1

HCID 12928524HCID 12928524, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

Reflux for 4 hours, a solution of 52.0 g (0.18 moles) of the product of step C in a mixture of 96 ml of 37% formaldehyde and 144 ml of 90% formic acid. Distill almost to dryness at 100° C. under reduced pressure (about 100 mm). Dissolve the residue in a mixture of 500 ml of 1 N sodium hydroxide and 500 ml of ethyl ether with cooling and stirring. Separate the ether layer, dry over anhydrous sodium sulfate, and evaporate to give (S)-7-chloro-8-methoxy-3-methyl-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine as a colorless solid. Obtain an analytically pure sample by crystallization from ethyl ether, m.p. 91°-92° C. [α]D26 =+47.3° (c=1, ethanol).

Workup

  1. temperatureReflux for 4 hours
  2. distillationDistill almost to dryness at 100° C. under reduced pressure (about 100 mm)
  3. dissolutionDissolve the residue
  4. additionin a mixture of 500 ml of 1 N sodium hydroxide and 500 ml of ethyl ether
  5. temperaturewith cooling
  6. customSeparate the ether layer
  7. dry with materialdry over anhydrous sodium sulfate
  8. customevaporate

Sources & evidence

ORD record
ord-a646f7aa4dcb45a4ad039a2e9e473e49
Source dataset
uspto-grants-1981_08
Patent number
US04284555

Reaction notes

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