Ammonia → HCID 69959201, compound

HRID 478667Notes

Reaction equation

HRID 478667 reaction equation
[CH:1]1([N:14]2[CH2:19][CH2:18][C:17](=O)[CH2:16][CH2:15]2)[C:12]2=[C:13]3[C:8](=[CH:9][CH:10]=[CH:11]2)[CH2:7][CH2:6][CH2:5][CH:4]3[CH2:3][CH2:2]1.[NH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C[Si]([C:32]#[N:33])(C)C.N>C(O)(=O)C>[CH:1]1([N:14]2[CH2:19][CH2:18][C:17]([NH:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)([C:32]#[N:33])[CH2:16][CH2:15]2)[C:12]2=[C:13]3[C:8](=[CH:9][CH:10]=[CH:11]2)[CH2:7][CH2:6][CH2:5][CH:4]3[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 6115AnilineHCID 82115Trimethylsilyl cyanideHCID 69959094HCID 69959094, compound

Product 1

HCID 69959201HCID 69959201, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

(1RS,3aRS)-1-(2,3,3a,4,5,6-Hexahydro-1H-phenalen-1-yl)-piperidin-4-one (2.62 g, 9.7 mmol) was dissolved in acetic acid (12 ml). Aniline (0.97 ml, 10.6 mmol) and trimethylsilylcyanide (1.2 ml, 9.7 mmol) were added and the mixture was stirred for 3 h at RT. The reaction mixture was poured into cold ammonia solution (40 ml), extracted with methylene chloride (2×200 ml) and brine (150 ml). The combined organic layers were combined, dried with magnesium sulfate and concentrated. Crystallization from diethylether/hexane yielded (1RS,3aRS)-1-(2,3,3a,4,5,6-Hexahydro-1H-phenalen-1-yl)-4-phenylamino-piperidine-4-carbonitrile (3.1 g, 86%) as a pale yellow solid, m.p. 142° C. and MS: m/e=372.4 (M+H+).

Workup

  1. extractionextracted with methylene chloride (2×200 ml) and brine (150 ml)
  2. dry with materialdried with magnesium sulfate
  3. concentrationconcentrated
  4. customCrystallization from diethylether/hexane

Sources & evidence

ORD record
ord-38fbaad20dbf400cb68e24db1453e879
Source dataset
uspto-grants-2003_11
Patent number
US06642247B2

Reaction notes

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