Water → HCID 19077550, compound

HRID 2256072Notes

Reaction equation

HRID 2256072 reaction equation
[C:1]1([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:5][C:4]([CH:7]=O)=[CH:3][CH:2]=1.[NH2:15][CH:16]1[CH:21]2[CH2:22][CH2:23][N:18]([CH2:19][CH2:20]2)[CH2:17]1.O>C1(C)C=CC=CC=1>[C:1]1([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:5][C:4]([CH:7]=[N:15][CH:16]2[CH:21]3[CH2:22][CH2:23][N:18]([CH2:19][CH2:20]3)[CH2:17]2)=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 962WaterHCID 76689(1,1'-Biphenyl)-4-carboxaldehydeHCID 1232383-Aminoquinuclidine

Product 1

HCID 19077550HCID 19077550, compoundYield 59.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-Biphenylcarboxaldehyde (160 mg) and 3-aminoquinuclidine (110 mg) were heated under reflux in toluene (50 ml) for 2 hours using a Dean and Stark water separator. The toluene was evaporated and the residue was purified by medium pressure column chromatography on alumina (ICN Alumina N 32-63), eluting with ethyl acetate to give 3-[(biphenyl-4-ylmethylene)amino]quinuclidine (150 mg) as a colourless solid, m.p. 82°-84° C.; microanalysis, found: C, 82.2; H, 7.7; N, 9.6%; C20H22N2 requires: C, 82.7; H, 7.6; N, 9.6%; NMR (CDCl3): 1.35-1.5(1H, m), 1.6-1.8(3H, m), 2.2-2.3(1H, m), 2.8-3.0(4H, m), 3.0-3.2(2H, m), 3.4-3.5(1H, m), 7.3-7.5(3H, m), 7.55-7.65(4H, m), 7.8(2H, dd) and 8.3(1H, s); m/z 291 (M+H).

Workup

  1. customThe toluene was evaporated
  2. customthe residue was purified by medium pressure column chromatography on alumina (ICN Alumina N 32-63)
  3. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-4c6cd532e0054645a07d731ae9e15b4a
Source dataset
uspto-grants-1997_08
Patent number
US05654315

Reaction notes

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