Ammonia → HCID 53792914, compound

HRID 1420672Notes

Reaction equation

HRID 1420672 reaction equation
[C@@H:1]1([N:10]2[CH2:15][CH2:14][C:13](=O)[CH2:12][CH2:11]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[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>[C@@H:1]1([N:10]2[CH2:15][CH2:14][C:13]([NH:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)([C:28]#[N:29])[CH2:12][CH2:11]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 6115AnilineHCID 82115Trimethylsilyl cyanideHCID 54250536HCID 54250536, compound

Product 1

HCID 53792914HCID 53792914, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

(S)-1-Indan-1-yl-piperidine-4-one (31 mmol) was dissolved in acetic acid (28 ml). Aniline (33 mmol) and trimethylsilylcyanide (31 mmol) were added and the mixture was stirred for 45 min. at room temperature. The reaction mixture was poured into cold ammonia solution (water/28% ammonia, 50 ml/30 ml). The solution was adjusted to pH 10 and extracted with methylene chloride. Organic phases were pooled, dried with sodium sulfate and concentrated. Crystallization from diethylether yielded the desired product as a solid. 8.1 g (80%) of (S)-1-indan-1-yl-4-phenylamino-piperidine-4-carbonitrile, m.p. 157-160° C. and MS: m/e=318.3 (M+H+).

Workup

  1. extractionextracted with methylene chloride
  2. dry with materialdried with sodium sulfate
  3. concentrationconcentrated
  4. customCrystallization from diethylether

Sources & evidence

ORD record
ord-e67e216faecd4597a465fb5937fb4402
Source dataset
uspto-grants-2000_06
Patent number
US06071925

Reaction notes

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