1-Benzylpiperazine → 1-Benzyl-4-[(1-t-butoxycarbonyl-4-piperidyl)carbonyl]piperazine

HRID 2288737Notes

Reaction equation

HRID 2288737 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:14]([O:18][C:19]([N:21]1[CH2:26][CH2:25][CH:24]([C:27](ON2C(=O)CCC2=O)=[O:28])[CH2:23][CH2:22]1)=[O:20])([CH3:17])([CH3:16])[CH3:15]>ClCCl>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:27]([CH:24]2[CH2:25][CH2:26][N:21]([C:19]([O:18][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:20])[CH2:22][CH2:23]2)=[O:28])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 759941-BenzylpiperazineHCID 15578030Succinimido 1-t-butoxycarbonylpiperidine-4-carboxylate

Product 1

HCID 40146251-Benzyl-4-[(1-t-butoxycarbonyl-4-piperidyl)carbonyl]piperazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-Benzylpiperazine (40.0 ml) was added in one portion to a solution of succinimido 1-t-butoxycarbonylpiperidine-4-carboxylate (75.0 g) in dry dichloromethane (1600 ml). The solution was stirred at ambient temperature under an atmosphere of argon for 17 hours. The solution was washed with water (500 ml) and saturated brine (250 ml). The organic layer was dried (Na2SO4) and evaporated. The residual oil was purified by chromatography on alumina, eluting with dichloromethane to give 1-benzyl-4-[(1-t-butoxycarbonyl-4-piperidyl)carbonyl]piperazine as an oil;

Workup

  1. washThe solution was washed with water (500 ml) and saturated brine (250 ml)
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. customevaporated
  4. customThe residual oil was purified by chromatography on alumina
  5. washeluting with dichloromethane

Sources & evidence

ORD record
ord-5aa4818ba0ba4c588412a8deb95b3af8
Source dataset
uspto-grants-2000_07
Patent number
US06090813

Reaction notes

Loading…