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Hydrochloric Acid → 1'-[3-(3-chloro-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 1156771
Notes
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Reaction equation

HRID 1156771 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[N:7]([CH2:16][CH2:17][CH2:18][O:19]S(C)(=O)=O)[C:6]=2[CH:24]=1.[O:25]=[C:26]1[C:34]2([CH2:39][CH2:38][NH:37][CH2:36][CH2:35]2)[N:29]2[CH2:30][CH2:31][CH2:32][CH2:33][CH:28]2[NH:27]1.C(=O)([O-])[O-].[K+].[K+].[ClH:46]>C(O)C.CO.O>[OH2:19].[ClH:1].[ClH:46].[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[N:7]([CH2:16][CH2:17][CH2:18][N:37]3[CH2:38][CH2:39][C:34]4([N:29]5[CH2:30][CH2:31][CH2:32][CH2:33][CH:28]5[NH:27][C:26]4=[O:25])[CH2:35][CH2:36]3)[C:6]=2[CH:24]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 130027121,2,3,5,6,7,8,8a-Octahydro-2-oxoimidazo[1,2-a]pyridine-3-spiro-4'-piperidineHCID 205339663-chloro-5-(3-methylsulfonyloxypropyl)-10,11-dihydro-5H-dibenz[b,f]azepine

Product 1

HCID 70480502
1'-[3-(3-chloro-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

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 5 g of 3-chloro-5-(3-methylsulfonyloxypropyl)-10,11-dihydro-5H-dibenz[b,f]azepine, 4 g of 1,2,3,5,6,7,8,8a-octahydro-2-oxoimidazo[1,2-a]pyridine-3-spiro-4'-piperidine, 4 g of potassium carbonate and 4 g of water in 40 ml of ethanol is stirred at 60° C. for 4 hours. The upper layer is separated and concentrated, and the residue is dissolved in 100 ml of toluene. The toluene solution is washed with water, dried, concentrated to about 15 ml and allowed to stand. The precipitated crystals are collected by filtration and recrystallized from ethanol. The crystals thus obtained are dissolved in methanol, and methanolic hydrochloric acid is added to give 1'-[3-(3-chloro-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, m.p. 261° C. This product is dried at 120° C. under reduced pressure for 4 hours to give the anhydrous product as white crystals, m.p. 271° C., 4.3 g.

Workup

  1. customThe upper layer is separated
  2. concentrationconcentrated
  3. dissolutionthe residue is dissolved in 100 ml of toluene
  4. washThe toluene solution is washed with water
  5. customdried
  6. concentrationconcentrated to about 15 ml
  7. filtrationThe precipitated crystals are collected by filtration
  8. customrecrystallized from ethanol
  9. customThe crystals thus obtained

Sources & evidence

ORD record
ord-0957372320ad4ccf942f9fd35732ac7e
Source dataset
uspto-grants-1982_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04337260

Reaction notes

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