Hydrochloric Acid → 1'-[3-(3-chloro-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)propyl]-1,2,3,5,6,7,8,8a-octahydro-2-oxo-imidazo[1,2-a]-pyridine-3-spiro-4'-piperidine dihydrochloride

HRID 1156772Notes

Reaction equation

HRID 1156772 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:11][CH2:10][C:9]3[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=3[C:7](=[CH:16][CH2:17][CH2:18]Br)[C:6]=2[CH:20]=1.[O:21]=[C:22]1[C:30]2([CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)[N:25]2[CH2:26][CH2:27][CH2:28][CH2:29][CH:24]2[NH:23]1.[ClH:36]>C(O)C>[ClH:1].[ClH:36].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:11][CH2:10][C:9]3[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=3[C:7](=[CH:16][CH2:17][CH2:18][N:33]3[CH2:32][CH2:31][C:30]4([N:25]5[CH2:26][CH2:27][CH2:28][CH2:29][CH:24]5[NH:23][C:22]4=[O:21])[CH2:35][CH2:34]3)[C:6]=2[CH:20]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 130027121,2,3,5,6,7,8,8a-Octahydro-2-oxoimidazo[1,2-a]pyridine-3-spiro-4'-piperidineHCID 544316363-chloro-5-(3-bromopropylidene)-10,11-dihydro-5H-dibenz[a,d]cycloheptene

Product 1

HCID 705366691'-[3-(3-chloro-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)propyl]-1,2,3,5,6,7,8,8a-octahydro-2-oxo-imidazo[1,2-a]-pyridine-3-spiro-4'-piperidine dihydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A mixture of 3.0 g of 3-chloro-5-(3-bromopropylidene)-10,11-dihydro-5H-dibenz[a,d]cycloheptene and 3.0 g of 1,2,3,5,6,7,8,8a-octahydro-2-oxoimidazo[1,2-a]pyridine-3-spiro-4'-piperidine in 20 ml of ethanol is boiled under reflux with stirring for 5 hours. The ethanol is then distilled off under reduced pressure, and the residue is dissolved in 30 ml of toluene. The toluene solution is washed with water and extracted with 30 ml of 5% hydrochloric acid. The aqueous layer is treated with activated charcoal and made alkaline. The separated oil is allowed to stand. The crystals thus obtained is dissolved in ethanol, and ethanolic hydrochloric acid is added to give 2.8 g of 1'-[3-(3-chloro-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)propyl]-1,2,3,5,6,7,8,8a-octahydro-2-oxo-imidazo[1,2-a]-pyridine-3-spiro-4'-piperidine dihydrochloride as white crystals, m.p. 262° C.

Workup

  1. temperatureunder reflux
  2. distillationThe ethanol is then distilled off under reduced pressure
  3. dissolutionthe residue is dissolved in 30 ml of toluene
  4. washThe toluene solution is washed with water
  5. extractionextracted with 30 ml of 5% hydrochloric acid
  6. additionThe aqueous layer is treated with activated charcoal
  7. customThe crystals thus obtained

Sources & evidence

ORD record
ord-daa8a8fb494445eba49f73e0b93ffecf
Source dataset
uspto-grants-1982_06
Patent number
US04337260

Reaction notes

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