Hydrochloride methanol → (2S,3S)-3-[(7-Methoxy-4,5-dihydro-[1,2,3,4]tetrazolo[1,5-a]quinolin-8-yl)methyl]amino-2-phenylpiperidine dihydrochloride

HRID 1740735Notes

Reaction equation

HRID 1740735 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH2:11][C@H:10]([NH:14][CH2:15][C:16]2[CH:25]=[C:24]3[C:19]([CH2:20][CH2:21][C:22]4[N:23]3[N:26]=[N:27][N:28]=4)=[CH:18][C:17]=2[O:29][CH3:30])[C@@H:9]1[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=O)(C)(C)C.[ClH:37].CO>CCOC(C)=O>[ClH:37].[ClH:37].[CH3:30][O:29][C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][C:16]=1[CH2:15][NH:14][C@H:10]1[CH2:11][CH2:12][CH2:13][NH:8][C@H:9]1[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[N:23]1[N:26]=[N:27][N:28]=[C:22]1[CH2:21][CH2:20]2

Participants

4

Reactant 2

HCID 21893726Hydrochloride methanolHCID 57252196(2S,3S)-1-tert-Butoxycarbonyl-3-[(7-methoxy-4,5-dihydro-[1,2,3,4]tetrazolo[1,5-a]quinolin-8-yl)methyl]amino-2-phenylpiperidine

Product 1

HCID 70278554(2S,3S)-3-[(7-Methoxy-4,5-dihydro-[1,2,3,4]tetrazolo[1,5-a]quinolin-8-yl)methyl]amino-2-phenylpiperidine dihydrochlorideYield 61%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of Compound 7 (110 mg, 0.23 mmol) in AcOEt (6 ml) was added an excess amount of HCl-MeOH, and stirred for 1 day. After the solvent was evaporated, the residual solid was recrystallized from MeOH-Et2O. The crystals precipitated were collected by filtration, washed with Et2O, and dried in vacuo at 30° C. to give Compound 8 (65 mg, 0.14 mmol, 61%) as a white solid.

Workup

  1. customAfter the solvent was evaporated
  2. customthe residual solid was recrystallized from MeOH-Et2O
  3. customThe crystals precipitated
  4. filtrationwere collected by filtration
  5. washwashed with Et2O
  6. customdried in vacuo at 30° C.

Sources & evidence

ORD record
ord-ebcb9f19a61e490fb88909ededf8176b
Source dataset
uspto-grants-1999_10
Patent number
US05972930

Reaction notes

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