Hydrochloric Acid → HCID 16038376, compound

HRID 2246718Notes

Reaction equation

HRID 2246718 reaction equation
C(O[C:6]([N:8](C)[CH2:9][CH2:10][C@@H:11]([N:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:20]2([CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)[C:19]1=[O:32])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=O)(C)(C)C.Cl.C(OCC)(=O)C>CCOCC>[CH3:6][NH:8][CH2:9][CH2:10][C@@H:11]([N:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:20]2([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]2)[C:19]1=[O:32])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 86611663HCID 86611663, compound

Product 1

HCID 16038376HCID 16038376, compoundYield 95.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

1′-[(1R)-3-(tert-butoxycarbonyl-methylamino)-1-phenylpropyl] spiro [cyclohexane-1,3′-indol]-2′(1′H)-one (70 mg, 0.15 mmol) was dissolved in ether (5 mL) and 2N HCl in ethyl acetate (0.3 mL, 0.6 mmol) was added. The mixture was stirred 16 hours then concentrated under a stream of nitrogen. The residue was purified via chromatography (silica, 5% methanol saturated with ammonia in chloroform) to give 50 mg of 1′-[(1R)-3-(methylamino)-1-phenylpropyl]spiro[cyclohexane-1,3′-indol]-2′(1′H)-one. The freebase was dissolved in ether (2 mL) and treated with 1N hydrochloric acid in ether (0.14 mL, 0.14 mmol, 1 equivalent). The white precipitate was collected and dried under vacuum to give 56 mg of 1′-[(1R)-3-(methylamino)-1-phenylpropyl]spiro[cyclohexane-1,3′-indol]-2′(1′H)-one hydrochloride.

Workup

  1. concentrationthen concentrated under a stream of nitrogen
  2. customThe residue was purified via chromatography (silica, 5% methanol saturated with ammonia in chloroform)

Sources & evidence

ORD record
ord-b34dfe1a433049dab762d0dbdafd0a08
Source dataset
uspto-grants-2010_03
Patent number
US07687529B2

Reaction notes

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