Potassium Carbonate → 1'-[3-(10,11-dihydro-5H-dibenz[b,f]azepin-5-yl)propyl]-1,2,3,5,6,7,8,8a-octahydro-2-oxo-imidazo[1,2-a]pyridine-3-spiro-4'-piperidine dihydrochloride monohydrate

HRID 1156770Notes

Reaction equation

HRID 1156770 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][N:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[CH2:9][CH2:8][C:7]2[CH:16]=[CH:17][CH:18]=[CH:19][C:6]1=2.[O:20]=[C:21]1[C:29]2([CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)[N:24]2[CH2:25][CH2:26][CH2:27][CH2:28][CH:23]2[NH:22]1.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[OH2:20].[ClH:1].[ClH:1].[CH:16]1[C:7]2[CH2:8][CH2:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:5]([CH2:4][CH2:3][CH2:2][N:32]3[CH2:31][CH2:30][C:29]4([N:24]5[CH2:25][CH2:26][CH2:27][CH2:28][CH:23]5[NH:22][C:21]4=[O:20])[CH2:34][CH2:33]3)[C:6]=2[CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2867795-(3-Chloropropyl)-10,11-dihydro-5H-dibenz[b,f]azepineHCID 130027121,2,3,5,6,7,8,8a-Octahydro-2-oxoimidazo[1,2-a]pyridine-3-spiro-4'-piperidine

Product 1

HCID 128312411'-[3-(10,11-dihydro-5H-dibenz[b,f]azepin-5-yl)propyl]-1,2,3,5,6,7,8,8a-octahydro-2-oxo-imidazo[1,2-a]pyridine-3-spiro-4'-piperidine dihydrochloride monohydrateYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 23 g of 5-(3-chloropropyl)-10,11-dihydro-5H-dibenz[b,f]azepine, 15 g of 1,2,3,5,6,7,8,8a-octahydro-2-oxo-imidazo[1,2-a]pyridine-3-spiro-4'-piperidine and 10 g of anhydrous potassium carbonate in 100 ml of ethanol is boiled under reflux for 48 hours. The ethanol is then distilled off under reduced pressure. The residue is added to 80 ml of toluene, and the insoluble matter is filtered off. The filtrate is washed with two 50 ml portions of water, and alcoholic hydrochloric acid is added. The precipitated crystals are collected by filtration and recrystallized from methanol to give 1'-[3-(10,11-dihydro-5H-dibenz[b,f]azepin-5-yl)propyl]-1,2,3,5,6,7,8,8a-octahydro-2-oxo-imidazo[1,2-a]pyridine-3-spiro-4'-piperidine dihydrochloride monohydrate as white crystals, m.p. 258° C., 70% yield.

Workup

  1. temperatureunder reflux for 48 hours
  2. distillationThe ethanol is then distilled off under reduced pressure
  3. additionThe residue is added to 80 ml of toluene
  4. filtrationthe insoluble matter is filtered off
  5. washThe filtrate is washed with two 50 ml portions of water, and alcoholic hydrochloric acid
  6. additionis added
  7. filtrationThe precipitated crystals are collected by filtration
  8. customrecrystallized from methanol

Sources & evidence

ORD record
ord-0e82f1d9323948d2a4f1612cf807e026
Source dataset
uspto-grants-1982_06
Patent number
US04337260

Reaction notes

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