Benzyl chloroformate → HCID 54373813, compound

HRID 2267233Notes

Reaction equation

HRID 2267233 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[NH:12]1[CH2:17][CH2:16][CH:15]([N:18]2[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]2)[CH2:14][CH2:13]1.C(N(C(C)C)C(C)C)C>C(Cl)Cl>[CH2:5]([O:4][C:2]([N:12]1[CH2:17][CH2:16][CH:15]([N:18]2[CH2:19][CH2:20][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:22][CH2:23]2)[CH2:14][CH2:13]1)=[O:3])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 17750356tert-Butyl 4-(piperidin-4-yl)piperazine-1-carboxylate

Product 1

HCID 54373813HCID 54373813, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 7.18 mL (48.0 mmol) benzyl chloroformate in 50 mL DCM was added dropwise to 12.3 g (45.7 mmol) tert-butyl 4-piperidin-4-yl-piperazine-1-carboxylate and 8.2 mL (50 mmol) N-ethyldiisopropylamine in 200 mL DCM while cooling with ice and the reaction mixture was stirred overnight at RT. It was washed with 200 mL of 15% K2CO3 solution, the organic phase was separated off and dried over Na2SO4. After elimination of the desiccant and solvent the residue was further reacted without any further purification.

Workup

  1. temperaturewhile cooling with ice
  2. washIt was washed with 200 mL of 15% K2CO3 solution
  3. customthe organic phase was separated off
  4. dry with materialdried over Na2SO4
  5. customAfter elimination of the desiccant and solvent the residue was further reacted without any further purification

Sources & evidence

ORD record
ord-be0c3b89c1734c5786e27b059de00b00
Source dataset
uspto-grants-2010_12
Patent number
US07858622B2

Reaction notes

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