1-Methylpiperazine → HCID 178480926, compound

HRID 1852546Notes

Reaction equation

HRID 1852546 reaction equation
[C:1]([O:5][C:6](=[O:19])[NH:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([NH:14][C:15](=[O:18])[CH2:16]Cl)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[CH3:20][N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1>C(Cl)Cl>[C:1]([O:5][C:6](=[O:19])[NH:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([NH:14][C:15](=[O:18])[CH2:16][N:24]2[CH2:25][CH2:26][N:21]([CH3:20])[CH2:22][CH2:23]2)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 178454048HCID 178454048, compound

Product 1

HCID 178480926HCID 178480926, compoundYield 59.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of trans-[4-(2-chloro-acetylamino)-cyclohexyl]-carbamic acid tert-butyl ester (330 mg, 1.14 mmol) in DCM (12 mL) was added to a solution of methylpiperazine (0.1 mL, 0.95 mmol) in DCM (1 mL) at RT. The resulting mixture was allowed to stir overnight, then diluted with DCM, and washed with a saturated aqueous solution of NaHCO3. The aqueous phase was extracted with DCM and then EtOAc. The combined organic phases were dried over Na2SO4, filtered and concentrated under reduced pressure to yield 199 mg of trans-{4-[2-(4-methyl-piperazin-1-yl)-acetylamino]-cyclohexyl}-carbamic acid tert-butyl ester without further purification.

Workup

  1. washwashed with a saturated aqueous solution of NaHCO3
  2. extractionThe aqueous phase was extracted with DCM
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8c8b6446cf8949349a41122fc7bf6dca
Source dataset
uspto-grants-2015_02
Patent number
US08962622B2

Reaction notes

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