Hydrochloric Acid → HCID 57863254, compound

HRID 2382995Notes

Reaction equation

HRID 2382995 reaction equation
Cl.[CH3:2][N:3]([CH3:35])[C:4]([N:6]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:8]2([CH2:13][CH2:12][N:11]([CH:14]3[CH2:20][CH:19]4[N:21](C(OC(C)(C)C)=O)[CH:16]([CH2:17][CH2:18]4)[CH2:15]3)[CH2:10][CH2:9]2)[CH2:7]1)=[O:5].O1CCOCC1.Cl>CO.CCOCC>[CH:19]12[NH:21][CH:16]([CH2:17][CH2:18]1)[CH2:15][CH:14]([N:11]1[CH2:10][CH2:9][C:8]3([C:29]4[C:34](=[CH:33][CH:32]=[CH:31][CH:30]=4)[N:6]([C:4]([N:3]([CH3:35])[CH3:2])=[O:5])[CH2:7]3)[CH2:13][CH2:12]1)[CH2:20]2

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-Dioxane2×HCID 86634251HCID 86634251, compound

Product 1

HCID 57863254HCID 57863254, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

Tert-butyl 3-(1-(dimethylcarbamoyl)spiro[indoline-3,4′-piperidine]-1′-yl)-8-azabicyclo[3.2.1]octane-8-carboxylate hydrochloride 6ac (0.850 g, 1.683 mmol) was dissolved in MeOH (5 mL) followed by dioxane (40 mL) and treated with 4N HCl in dioxane (4.21 mL, 16.83 mmol). The reaction was allowed to stir overnight (complete conversion). The mixture was diluted with Et2O (150 mL) and filtered. The precipitate was washed with EtOAc (3×30 mL) and dried to provide 1′-(8-azabicyclo[3.2.1]octan-3-yl)-N,N-dimethylspiro[indoline-3,4′-piperidine]-1-carboxamide 6ad bis-hydrochloride as an off white solid (95% purity by LC/MS). This material was used for the next step without further purification. LC/MS m/z 369.0 [M+H]+ retention time 1.04 minutes (10-99% CH3CN—H2O gradient with 0.03% TFA, 5 min)

Workup

  1. filtrationfiltered
  2. washThe precipitate was washed with EtOAc (3×30 mL)
  3. customdried

Sources & evidence

ORD record
ord-1a0069eaf9a84caf8b0249869fd3a572
Source dataset
uspto-grants-2012_09
Patent number
US08263605B2

Reaction notes

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