Diisopropylethylamine → HCID 66879305, compound

HRID 1878322Notes

Reaction equation

HRID 1878322 reaction equation
[C:1]([NH:5][C:6](=[O:15])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13]Cl)[CH:8]=1)([CH3:4])([CH3:3])[CH3:2].[N:16]1([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.C(N(C(C)C)C(C)C)C>CS(C)=O.C(OCC)(=O)C>[C:1]([NH:5][C:6]([C:7]1[CH:8]=[C:9]([CH:10]=[CH:11][CH:12]=1)[CH2:13][N:19]1[CH2:18][CH2:17][N:16]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:21][CH2:20]1)=[O:15])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 43156221N-tert-butyl-3-(chloromethyl)benzamide

Product 1

HCID 66879305HCID 66879305, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

The N-tert-butyl-3-(chloromethyl)benzamide was placed under an argon atmosphere and treated with a solution of tert-butyl 1-piperazine-carboxylate (2.96 g, 15.9 mmol) and N-ethyl-N-isopropylpropan-2-amine (5.53 mL, 31.7 mmol) in dimethyl sulfoxide (15 mL) at room temperature. The reaction mixture was stirred overnight, diluted with ethyl acetate (100 mL) and washed with saturated aqueous sodium chloride (×5). The organic phase was dried on magnesium sulfate, filtered and concentrated under vacuum to give a crude oil. This oil was purified by iterative rounds of silica chromatography (20-70% ethyl acetate in n-hexanes, followed by 0-6% methanol in dichloromethane) to give the intermediate tert-butyl 4-(3-(tert-butylcarbamoyl)benzyl)piperazine-1-carboxylate (5.04 g).

Workup

  1. washwashed with saturated aqueous sodium chloride (×5)
  2. customThe organic phase was dried on magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. customto give a crude oil
  6. customThis oil was purified by iterative rounds of silica chromatography (20-70% ethyl acetate in n-hexanes, followed by 0-6% methanol in dichloromethane)

Sources & evidence

ORD record
ord-7527f9fa96a84bbea3a01f23dec23fb6
Source dataset
uspto-grants-2012_11
Patent number
US08314091B2

Reaction notes

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