HCID 19608161, compound → HCID 19607843, compound

HRID 1291627Notes

Reaction equation

HRID 1291627 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:36]=[CH:35][CH:34]=[CH:33][C:10]=1[C:11]([NH:13][C:14]1[CH:32]=[CH:31][C:17]([C:18]([N:20]2[C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=3[CH2:24][CH2:23][CH2:22][CH2:21]2)=[O:19])=[CH:16][CH:15]=1)=[O:12].[C:37]1(=[O:47])[NH:41][C:40](=[O:42])[C:39]2=[CH:43][CH:44]=[CH:45][CH:46]=[C:38]12.[K]>CN(C)C=O>[C:37]1(=[O:47])[N:41]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]2[CH:36]=[CH:35][CH:34]=[CH:33][C:10]=2[C:11]([NH:13][C:14]2[CH:32]=[CH:31][C:17]([C:18]([N:20]3[C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=4[CH2:24][CH2:23][CH2:22][CH2:21]3)=[O:19])=[CH:16][CH:15]=2)=[O:12])[C:40](=[O:42])[C:39]2=[CH:43][CH:44]=[CH:45][CH:46]=[C:38]12

Participants

4

Reactant 2

HCID 19608161HCID 19608161, compoundHCID 24194345Phthalimide potassium salt

Product 1

HCID 19607843HCID 19607843, compoundYield 90.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1-{4-[2-(6-bromohexyloxy)benzoylamino]benzoyl}-2,3,4,5-tetrahydro-1H-benzazepine (4.00 g), potassium phthalimide (2.02 g) and dimethylformamide (100 ml) is stirred at 100° C. for 5 hours. The reaction mixture is filtered and the filtrate is distilled off. The resulting residue is extracted with ethyl acetate and the organic layer is washed successively with water and saturated saline solution, and dried over magnesium sulfate. The solvent is distilled off and the resulting residue is purified by silica gel column chromatography (eluent; dichloromethane), and recrystallized from methanol/diethyl ether to give 1-{4-[2-(6-phthalimidohexyloxy)benzoylamino]benzoyl}-2,3,4,5-tetrahydro-1H-benzazepine (4.06 g) as white powder, m.p. 145°-146.5° C.

Workup

  1. filtrationThe reaction mixture is filtered
  2. distillationthe filtrate is distilled off
  3. extractionThe resulting residue is extracted with ethyl acetate
  4. washthe organic layer is washed successively with water and saturated saline solution
  5. dry with materialdried over magnesium sulfate
  6. distillationThe solvent is distilled off
  7. customthe resulting residue is purified by silica gel column chromatography (eluent; dichloromethane)
  8. customrecrystallized from methanol/diethyl ether

Sources & evidence

ORD record
ord-d5634de3c08049218578cee440fa6481
Source dataset
uspto-grants-1998_05
Patent number
US05753677

Reaction notes

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