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Hydrochloric Acid → (R)-1-(3-(9H-Tribenz[b,d,f]azepine-9-yl)propyl)-3-piperidinecarboxylic acid, hydrochloride

HRID 861899
Notes
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Reaction equation

HRID 861899 reaction equation
[ClH:1].C([O:4][C:5]([C@@H:7]1[CH2:12][CH2:11][CH2:10][N:9]([CH2:13][CH2:14][CH2:15][N:16]2[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[C:20]3[CH:27]=[CH:28][CH:29]=[CH:30][C:19]=3[C:18]3[CH:31]=[CH:32][CH:33]=[CH:34][C:17]2=3)[CH2:8]1)=[O:6])C.Cl>C(O)C.[OH-].[Na+]>[ClH:1].[CH:30]1[C:19]2[C:18]3[CH:31]=[CH:32][CH:33]=[CH:34][C:17]=3[N:16]([CH2:15][CH2:14][CH2:13][N:9]3[CH2:10][CH2:11][CH2:12][C@@H:7]([C:5]([OH:6])=[O:4])[CH2:8]3)[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[C:20]=2[CH:27]=[CH:28][CH:29]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 70197521(R)-1-(3-(9H-tribenz[b,d,f]azepin-9-yl)propyl)-3-piperidine carboxylic acid ethyl ester hydrochloride

Product 1

HCID 131720461(R)-1-(3-(9H-Tribenz[b,d,f]azepine-9-yl)propyl)-3-piperidinecarboxylic acid, hydrochlorideYield 74.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×
HCID 14798
Sodium Hydroxide
Solvent

Procedure

The above ester (0.13 g, 0.27 mmol) was dissolved in ethanol (3 ml) and 2N sodium hydroxide (0.6 ml). The mixture was stirred at room temperature for 1.5 hour, acidified by addition of 1N hydrochloric acid (pH 1) and ethanol was removed in vacuo. The aqueous solution was diluted with water (10 ml), washed with diethyl ether (20 ml) and extracted with dichloromethane (30 ml). The organic extract was dried (MgSO4) and concentrated in vacuo to afford 90 mg (74%) of the title compound as a solid.

Workup

  1. customwas removed in vacuo
  2. additionThe aqueous solution was diluted with water (10 ml)
  3. washwashed with diethyl ether (20 ml)
  4. extractionextracted with dichloromethane (30 ml)
  5. extractionThe organic extract
  6. dry with materialwas dried (MgSO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-77571e7262b9455bb2c38e4b470233f3
Source dataset
uspto-grants-1998_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05716949

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes