Diisopropylethylamine → 3,4-Dichlorophenyl 4-[(1-methylpiperidin-3-yl)methyl]piperazine-1-carboxylate

HRID 2371134Notes

Reaction equation

HRID 2371134 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[C:7]([Cl:12])[CH:6]=1)=[O:3].[CH3:13][N:14]1[CH2:19][CH2:18][CH2:17][CH:16]([CH2:20][N:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)[CH2:15]1.C(N(CC)C(C)C)(C)C.C(=O)(O)[O-].[Na+]>ClCCl>[CH3:13][N:14]1[CH2:19][CH2:18][CH2:17][CH:16]([CH2:20][N:21]2[CH2:26][CH2:25][N:24]([C:2]([O:4][C:5]3[CH:10]=[CH:9][C:8]([Cl:11])=[C:7]([Cl:12])[CH:6]=3)=[O:3])[CH2:23][CH2:22]2)[CH2:15]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 27369401-[(1-Methylpiperidin-3-yl)methyl]piperazineHCID 1307789072305-24-9

Product 1

HCID 576567323,4-Dichlorophenyl 4-[(1-methylpiperidin-3-yl)methyl]piperazine-1-carboxylateYield 60.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3,4-Dichlorophenyl chloroformate (282 mg) in dichloromethane (10 ml) was added to a solution of 1-[(1-methylpiperidin-3-yl)methyl]piperazine (246 mg) in dichloromethane (2 ml) at room temperature. N,N-Diisopropylethylamine (0.44 ml) was added and the mixture stirred for 18 hours. Saturated aqueous sodium bicarbonate solution (5 ml) was added and the dichloromethane layer separated then concentrated in vacuo onto silica gel (0.5 g). The resulting powder was subjected to chromatography on silica gel (20 g) using a gradient of 100% dichloromethane through to 20% methanolic ammonia in dichloromethane to give the title compound (292 mg).

Workup

  1. customthe dichloromethane layer separated
  2. concentrationthen concentrated in vacuo onto silica gel (0.5 g)

Sources & evidence

ORD record
ord-65f958bc4af24553b7b772b49832bf1f
Source dataset
uspto-grants-2014_04
Patent number
US08710224B2

Reaction notes

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