N-(3-tert-butoxycarbonylaminopropyl)-4-cyano-4-(o-tolyl)piperidine → N-(3-aminopropyl)-4-cyano-4-(o-tolyl)piperidine

HRID 650527Notes

Reaction equation

HRID 650527 reaction equation
C(OC([NH:8][CH2:9][CH2:10][CH2:11][N:12]1[CH2:17][CH2:16][C:15]([C:25]#[N:26])([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[CH3:24])[CH2:14][CH2:13]1)=O)(C)(C)C.Cl.CCOC(C)=O>C(OCC)(=O)C>[NH2:8][CH2:9][CH2:10][CH2:11][N:12]1[CH2:13][CH2:14][C:15]([C:25]#[N:26])([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[CH3:24])[CH2:16][CH2:17]1

Participants

4

Reactant 2

HCID 21712249N-(3-tert-butoxycarbonylaminopropyl)-4-cyano-4-(o-tolyl)piperidineHCID 21866389Hydrogen chloride-ethyl acetate

Product 1

HCID 21712244N-(3-aminopropyl)-4-cyano-4-(o-tolyl)piperidine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 25 (7.90 g, 22.0 mmol) in ethyl acetate (200 mL) was cooled to 0° C. and treated with sat'd HCl/EtOAc solution (200 mL). The mixture was stirred at room temperature (1 h). The solvent was partially removed in vacuo and the mixture diluted with ethyl acetate and sodium carbonate solution. The aqueous layer was extracted with two additional portions of ethyl acetate and three portions of dichloromethane. The combined organic extracts were washed with brine, dried over Na2SO4, and concentrated under reduced pressure to afford the title compound (26). The crude product was used directly.

Workup

  1. customThe solvent was partially removed in vacuo
  2. additionthe mixture diluted with ethyl acetate and sodium carbonate solution
  3. extractionThe aqueous layer was extracted with two additional portions of ethyl acetate and three portions of dichloromethane
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2a15d1514b3740c0a4f5b3d90bc02c40
Source dataset
uspto-grants-2001_08
Patent number
US06274583B1

Reaction notes

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