Acetic Acid → HCID 18001088, compound

HRID 1249987Notes

Reaction equation

HRID 1249987 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([C:12](=[O:22])[CH:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]3([O:20][CH3:21])N)[CH2:10][CH2:9][CH2:8][CH:7]([CH2:23][C:24]([N:26]3[CH2:31][CH2:30][N:29]([CH3:32])[CH2:28][CH2:27]3)=[O:25])[C:6]=2[CH:33]=1.[C:34]1([CH3:42])[C:35]([CH:40]=O)=[CH:36][CH:37]=[CH:38][CH:39]=1.C(O)(=O)C.C([BH3-])#[N:48].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([C:12](=[O:22])[C:13]3[CH:18]=[CH:17][C:16]([NH:48][CH2:40][C:35]4[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=4[CH3:42])=[CH:15][C:14]=3[O:20][CH3:21])[CH2:10][CH2:9][CH2:8][CH:7]([CH2:23][C:24]([N:26]3[CH2:27][CH2:28][N:29]([CH3:32])[CH2:30][CH2:31]3)=[O:25])[C:6]=2[CH:33]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 107222-MethylbenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 18001077HCID 18001077, compound

Product 1

HCID 18001088HCID 18001088, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of 7-chloro-5-[(4-methyl-1-piperazinyl)carbonylmethyl]-1-(2-methoxy-2-aminobenzoyl)-2,3,4,5-tetrahydro-1H-benzazepine (0.8 g) in methanol (30 ml) are added o-tolualdehyde (0.35 ml) and acetic acid (1 ml), and the mixture is stirred at 50-60° C. for 2-3 hours. To the mixture is added sodium cyanoborohydride (0.11 g) at room temperature, and the mixture is stirred for two hours. The mixture is evaporated to remove the solvent, and to the residue is added water. The mixture is extracted with ethyl acetate, and the extract is dried, and evaporated. The residue is purified by silica gel column chromatography (solvent; dichloromethane:methanol=50:1→25:1), and recrystallized from acetone/diethyl ether to give 7-chloro-5-[(4-methyl-1-piperazinyl)carbonylmethyl]-1-[2-methoxy-4-(2-methylbenzylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.71 g) as white powder.

Workup

  1. stirringthe mixture is stirred for two hours
  2. customThe mixture is evaporated
  3. customto remove the solvent
  4. additionto the residue is added water
  5. extractionThe mixture is extracted with ethyl acetate
  6. customthe extract is dried
  7. customevaporated
  8. customThe residue is purified by silica gel column chromatography (solvent; dichloromethane:methanol=50:1→25:1)
  9. customrecrystallized from acetone/diethyl ether

Sources & evidence

ORD record
ord-c45fb2152bc147f4a2ebf7a954e8f449
Source dataset
uspto-grants-2002_01
Patent number
US06335327B1

Reaction notes

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