Acetyl chloride → N-Methyl-1-((2-(pyrrolidin-1-yl)pyridin-4-yl)methyl)piperidin-4-amine hydrochloride

HRID 1193318Notes

Reaction equation

HRID 1193318 reaction equation
[CH3:1][N:2]([CH:10]1[CH2:15][CH2:14][N:13]([CH2:16][C:17]2[CH:22]=[CH:21][N:20]=[C:19]([N:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[CH:18]=2)[CH2:12][CH2:11]1)C(=O)OC(C)(C)C.C([Cl:31])(=O)C>C(O)C>[ClH:31].[CH3:1][NH:2][CH:10]1[CH2:15][CH2:14][N:13]([CH2:16][C:17]2[CH:22]=[CH:21][N:20]=[C:19]([N:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[CH:18]=2)[CH2:12][CH2:11]1

Participants

4

Reactant 2

HCID 6367Acetyl chloride2×HCID 66805506tert-Butyl methyl(1-((2-(pyrrolidin-1-yl)pyridin-4-yl)methyl)piperidin-4-yl)carbamate

Product 1

HCID 66799205N-Methyl-1-((2-(pyrrolidin-1-yl)pyridin-4-yl)methyl)piperidin-4-amine hydrochlorideYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

tert-Butyl methyl(1-((2-(pyrrolidin-1-yl)pyridin-4-yl)methyl)piperidin-4-yl)carbamate (1.469 mmol, 1.0 eq) was dissolved in ethanol (5 ml), and acetyl chloride (7.345 mmol, 5 eq) was added, while cooling with ice. The reaction mixture was stirred for 16 h at RT. TLC monitoring showed that the reaction was incomplete. Acetyl chloride (1 eq) was metered in, and the reaction mixture was stirred for 1 h at 50° C. A solid precipitated. Ethanol was concentrated slightly, and the precipitate was filtered off, washed with diethyl ether and dried. Yield: >99%

Workup

  1. temperaturewhile cooling with ice
  2. stirringwas stirred for 1 h at 50° C
  3. customA solid precipitated
  4. concentrationEthanol was concentrated slightly
  5. filtrationthe precipitate was filtered off
  6. washwashed with diethyl ether
  7. customdried

Sources & evidence

ORD record
ord-3dec3ec4ce294b07ad522203dc326bc7
Source dataset
uspto-grants-2014_03
Patent number
US08680159B2

Reaction notes

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