Ammonia → HCID 23298864, compound

HRID 1952686Notes

Reaction equation

HRID 1952686 reaction equation
[CH:1]12[CH:9]([N:10]3[CH2:15][CH2:14][C:13](=O)[CH2:12][CH2:11]3)[CH:5]([CH2:6][CH2:7][CH2:8]1)[CH2:4][CH2:3][CH2:2]2.[NH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C[Si]([C:28]#[N:29])(C)C.N>C(O)(=O)C>[CH:1]12[CH:9]([N:10]3[CH2:15][CH2:14][C:13]([NH:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)([C:28]#[N:29])[CH2:12][CH2:11]3)[CH:5]([CH2:6][CH2:7][CH2:8]1)[CH2:4][CH2:3][CH2:2]2

Participants

6

Reactant 4

HCID 222AmmoniaHCID 6115AnilineHCID 82115Trimethylsilyl cyanideHCID 23298904HCID 23298904, compound

Product 1

HCID 23298864HCID 23298864, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1-Bicyclo[3.3.1]non-9-yl-piperidin-4-one (2.99 g, 13.5 mmol) was dissolved in acetic acid (15 ml). Aniline (1.36 ml, 14.9 mmol) and trimethylsilylcyanide (1.44 ml, 13.5 mmol) were added at 0° C. and the mixture was stirred for 17 h at room temperature. The reaction mixture was poured into cold ammonia solution (water/28% ammonia, 30 ml/50 ml) and extracted with dichloromethane (2×100 ml). The combined organic phases were washed with brine (100 ml), dried (MgSO4) and concentrated. Column chromatography on silica gel (toluene/ethyl acetate 4:1) yielded the desired product (3.18 g, 73%) as a pale yellow solid, m.p. 168° C., MS: m/e=324.4 (M+H+).

Workup

  1. extractionextracted with dichloromethane (2×100 ml)
  2. washThe combined organic phases were washed with brine (100 ml)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b2f9a6501c9744c7ba51c30f62fbd2e7
Source dataset
uspto-grants-2000_09
Patent number
US06113527

Reaction notes

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