Potassium Carbonate → HCID 21968990, compound

HRID 1420674Notes

Reaction equation

HRID 1420674 reaction equation
[C@H:1]1([NH2:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[I-].C([N+]1(C)[CH2:26][CH2:25][C:24](=[O:27])[CH2:23][CH2:22]1)C>C(O)C.O>[C@H:1]1([N:11]2[CH2:26][CH2:25][C:24](=[O:27])[CH2:23][CH2:22]2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 70580721-Aminotetralin, (R)-HCID 110975681-Ethyl-1-methyl-4-oxopiperidin-1-ium iodide

Product 1

HCID 21968990HCID 21968990, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

(R)-1,2,3,4-Tetrahydro-1-naphthylamine (16 mmol) was dissolved in ethanol (30 ml). Potassium carbonate (9.3 mmol) and 1-ethyl-1-methyl-4-oxo-piperidinium iodide (23 mmol) dissolved in water (30 ml) were added and the mixture was refluxed for 1 h. Water was added, ethanol was removed in vacuo and the residue was extracted with ethyl acetate. Organic phases were pooled, dried with sodium sulfate and concentrated. Chromatography on silica gel (ethyl acetate) yielded (R)-1-(1,2,3,4-tetrahydro-naphtalen-1-yl)-piperidine-4-one which was dissolved in acetic acid (11 ml). Aniline (14 mmol) and trimethylsilylcyanide (13 mmol) were added and the mixture was stirred for 1.5 h at room temperature. The reaction mixture was poured into cold ammonia solution (water/28% ammonia, 70 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 (R)4-phenylamino-1-(1,2,3,4-tetrahydro-naphtalen-1-yl)-piperidine-4-carbonitrile, m.p. 152-153° C. and MIS: m/e=332.3 (M+H+).

Workup

  1. additionwere added
  2. temperaturethe mixture was refluxed for 1 h
  3. customethanol was removed in vacuo
  4. extractionthe residue was extracted with ethyl acetate
  5. dry with materialdried with sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-fb9eecb1943a4cf6a3f524a170da5b93
Source dataset
uspto-grants-2000_06
Patent number
US06071925

Reaction notes

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