Sodium borohydride → HCID 9882536, compound

HRID 2256073Notes

Reaction equation

HRID 2256073 reaction equation
[BH4-].[Na+].[C:3]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:8]=[CH:7][C:6]([CH:9]=[N:10][CH:11]2[CH:16]3[CH2:17][CH2:18][N:13]([CH2:14][CH2:15]3)[CH2:12]2)=[CH:5][CH:4]=1>CO>[C:3]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:4]=[CH:5][C:6]([CH2:9][NH:10][CH:11]2[CH:16]3[CH2:17][CH2:18][N:13]([CH2:14][CH2:15]3)[CH2:12]2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 19077550HCID 19077550, compound

Product 1

HCID 9882536HCID 9882536, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (260 mg) was added to a stirred solution of 3-[(biphenyl-4-ylmethylene)amino]quinuclidine (990 mg) in methanol (50 ml) and the reaction mixture stirred for 2 hours. The methanol was evaporated and the residue dissolved in 1M hydrochloric acid (12 ml). The aqueous solution was washed with diethyl ether (3×25 ml) before the addition of excess sodium hydroxide solution (density 1.35 g/cm3) to pH 14. The mixture was extracted with diethyl ether, the ether separated, dried (Na2SO4) and evaporated. An excess of saturated ethereal hydrogen chloride was added to precipitate a solid which was crystallised from methanol/ethyl acetate to give 3-[(biphenyl-4-ylmethyl)amino]quinuclidine (820 mg) as a colourless solid, m.p. 180°-181° C., microanalysis, found: C, 62.8; H, 7.3; N, 7.4%; C20H24N2 2HCl.H2O requires: C, 62.7; H, 7.3; N, 7.3%; NMR: ([CD3 ]2SO): 1.7-2.0(3H, m), 2.2-2.4(1H, m), 2.6(1H, s), 3.1-3.8(8H, m) 4.2(2H, s), 7.3-7.5(3H, m) and 7.6-7.8(6H, m); m/z 293 (M+H).

Workup

  1. customThe methanol was evaporated
  2. dissolutionthe residue dissolved in 1M hydrochloric acid (12 ml)
  3. washThe aqueous solution was washed with diethyl ether (3×25 ml) before the addition of excess sodium hydroxide solution (density 1.35 g/cm3) to pH 14
  4. extractionThe mixture was extracted with diethyl ether
  5. customthe ether separated
  6. dry with materialdried (Na2SO4)
  7. customevaporated
  8. additionAn excess of saturated ethereal hydrogen chloride was added
  9. customto precipitate a solid which
  10. customwas crystallised from methanol/ethyl acetate

Sources & evidence

ORD record
ord-2ce61cca82534358a0d4e4eb80dfcf5c
Source dataset
uspto-grants-1997_08
Patent number
US05654315

Reaction notes

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