HCID 54349531, compound → HCID 22993541, compound

HRID 1275240Notes

Reaction equation

HRID 1275240 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][C:14]([C:25]#[N:26])([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=2[Cl:24])[CH2:13][CH2:12]1)(C)(C)C>ClCCl.FC(F)(F)C(O)=O>[NH2:7][CH2:8][CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][C:14]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=2[Cl:24])([C:25]#[N:26])[CH2:13][CH2:12]1

Participants

4

Reactant 1

HCID 54349531HCID 54349531, compound

Product 1

HCID 22993541HCID 22993541, compoundYield 95.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To 3-[4-cyano-4-(2,4-dichlorophenyl)-piperidin-1-yl]-propyl-carbamic acid tert-butyl ester (0.589, 1.42 mmol) in dichloromethane (5 mL), trifluoroacetic acid (1 mL) was added and the solution stirred at room temperature for 1 hour. The solution was concentrated, neutralized with 10% KOH solution and extracted into 25 mL of dichloromethane. The organic layer was dried over sodium sulfate, filtered and concentrated to give 0.423 g (93%) of 1-(3-aminopropyl)-4-(2,4-dichlorophenyl)-piperidine-4-carbonitrile which was used as such for the subsequent step.

Workup

  1. concentrationThe solution was concentrated
  2. extractionextracted into 25 mL of dichloromethane
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-fc94475fb0474baa8c9c9907c4a77cc9
Source dataset
uspto-grants-2000_12
Patent number
US06159990

Reaction notes

Loading…