Hydrochloric Acid → 4-(3-Amino-8-azabicyclo[3.2.1]oct-8-yl)naphthalene-1-carbonitrile, hydrochloride

HRID 916324Notes

Reaction equation

HRID 916324 reaction equation
O=[C:2]1[CH2:8][CH:7]2[N:9]([C:10]3[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[C:13]([C:20]#[N:21])=[CH:12][CH:11]=3)[CH:4]([CH2:5][CH2:6]2)[CH2:3]1.C([O-])(=O)C.[NH4+].C([BH3-])#[N:28].[Na+].[ClH:31]>CO>[ClH:31].[NH2:28][CH:2]1[CH2:8][CH:7]2[N:9]([C:10]3[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[C:13]([C:20]#[N:21])=[CH:12][CH:11]=3)[CH:4]([CH2:5][CH2:6]2)[CH2:3]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 247436404-(3-Oxo-8-azabicyclo[3.2.1]octan-8-yl)naphthalene-1-carbonitrile

Product 1

HCID 1317266004-(3-Amino-8-azabicyclo[3.2.1]oct-8-yl)naphthalene-1-carbonitrile, hydrochlorideYield 36%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

156AF03-217 (252 mg, 0.912 mmol) was dissolved in methanol (25 mL). Ammonium acetate (702 mg, 9.12 mmol) and sodium cyanoborohydride (57.3 mg, 0.912 mmol) were added together with some molecular sieves (3 Å). This mixture was allowed to react at rt for 60 hours. Hydrochloric acid (2 M) was added until pH<2 and the mixture was washed with ethyl acetate (2×25 mL). The aqueous layer was made alkaline with sodium hydroxide and extracted with ethyl acetate (3×30 mL). The combined organic layers were evaporated to dryness and purified by ion-exchange (SCX) to give 90 mg (36%) of the title compound.

Workup

  1. customto react at rt for 60 hours
  2. washthe mixture was washed with ethyl acetate (2×25 mL)
  3. extractionextracted with ethyl acetate (3×30 mL)
  4. customThe combined organic layers were evaporated to dryness
  5. custompurified by ion-exchange (SCX)

Sources & evidence

ORD record
ord-20ff5d02b7bd41fcaab39fc58b6fde2c
Source dataset
uspto-grants-2007_09
Patent number
US07268232B2

Reaction notes

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