Acetic Acid → HCID 18001084, compound

HRID 1249989Notes

Reaction equation

HRID 1249989 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([C:12](=[O:21])[C:13]3[CH:18]=[CH:17][C:16]([CH:19]=O)=[CH:15][CH:14]=3)[CH2:10][CH2:9][CH2:8][CH:7]([CH2:22][C:23]([N:25]3[CH2:30][CH2:29][N:28]([CH3:31])[CH2:27][CH2:26]3)=[O:24])[C:6]=2[CH:32]=1.[C:33](O)(=O)[CH3:34].[C:37]([BH3-])#[N:38].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([C:12](=[O:21])[C:13]3[CH:14]=[CH:15][C:16]([CH2:19][NH:38][C:37]4[CH:6]=[CH:32][CH:2]=[CH:3][C:33]=4[CH3:34])=[CH:17][CH:18]=3)[CH2:10][CH2:9][CH2:8][CH:7]([CH2:22][C:23]([N:25]3[CH2:30][CH2:29][N:28]([CH3:31])[CH2:27][CH2:26]3)=[O:24])[C:6]=2[CH:32]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 18001053HCID 18001053, compound

Product 1

HCID 18001084HCID 18001084, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 7-chloro-5-[(4-methyl-1-piperazinyl)carbonylmethyl]-1-(4-formylbenzoyl)-2,3,4,5-tetrahydro-1H-benzazepine (0.29 g) in methanol (30 ml) are added o-toluizine (0.2 ml) and acetic acid until the mixture becomes pH 4. The mixture is heated with stirring at 50° C. for 8 hours, and thereto is added sodium cyanoborohydride (0.085 g) with ice-cooling, and the mixture is stirred for one hour. The mixture is evaporated to remove the methanol, and thereto is added water. The mixture is extracted with ethyl acetate, and the extract is washed with water, dried, and evaporated to remove the solvent. The residue is purified by silica gel column chromatography (solvent; dichloromethane:methanol=100:1→50:1) to give 7-chloro-5-[(4-methyl-1-piperazinyl)carbonylmethyl]-1-[4-(2-methylanilinomethyl)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.1 g) as colorless amorphous.

Workup

  1. temperatureThe mixture is heated
  2. temperaturecooling
  3. stirringthe mixture is stirred for one hour
  4. customThe mixture is evaporated
  5. customto remove the methanol
  6. additionis added water
  7. extractionThe mixture is extracted with ethyl acetate
  8. washthe extract is washed with water
  9. customdried
  10. customevaporated
  11. customto remove the solvent
  12. customThe residue is purified by silica gel column chromatography (solvent; dichloromethane:methanol=100:1→50:1)

Sources & evidence

ORD record
ord-2f81ba1f6a514abaac6bb239d272bcf3
Source dataset
uspto-grants-2002_01
Patent number
US06335327B1

Reaction notes

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