Ethanesulfonyl chloride → 4-(Cyclopropylmethyl)-1-(ethylsulfonyl)piperidine-4-carbonitrile

HRID 502892Notes

Reaction equation

HRID 502892 reaction equation
Cl.[CH:2]1([CH2:5][C:6]2([C:12]#[N:13])[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]2)[CH2:4][CH2:3]1.CCN(C(C)C)C(C)C.[CH2:23]([S:25](Cl)(=[O:27])=[O:26])[CH3:24]>C(Cl)Cl>[CH:2]1([CH2:5][C:6]2([C:12]#[N:13])[CH2:7][CH2:8][N:9]([S:25]([CH2:23][CH3:24])(=[O:27])=[O:26])[CH2:10][CH2:11]2)[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 11667Ethanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 686190964-(Cyclopropylmethyl)-piperidine-4-carbonitrile hydrochloride

Product 1

HCID 594281864-(Cyclopropylmethyl)-1-(ethylsulfonyl)piperidine-4-carbonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of 4-(cyclopropylmethyl)piperidine-4-carbonitrile hydrochloride (I-3, 2.5 g, 12.5 mmol) in CH2Cl2 (130 mL) at 0° C. was treated with i-Pr2NEt (8.7 mL, 50 mmol) and EtSO2Cl (1.8 mL, 18.7 mmol) dropwise. After 2 h, the reaction was quenched with the addition of 1 M aqueous NaOH (40 mL) and stirred 18 h before being extracted with CH2Cl2 (3×50 mL). The combined organic extracts were dried (Na2SO4) and concentrated under reduced pressure to afford 4-(cyclopropylmethyl)-1-(ethylsulfonyl)piperidine-4-carbonitrile (I-4, M+H+=256.1) as an off-white amorphous solid. This material was used in subsequent reactions without further purification.

Workup

  1. customthe reaction was quenched with the addition of 1 M aqueous NaOH (40 mL)
  2. extractionbefore being extracted with CH2Cl2 (3×50 mL)
  3. dry with materialThe combined organic extracts were dried (Na2SO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c91641ad0fb748c6bb65a1a924730520
Source dataset
uspto-grants-2010_08
Patent number
US07776886B2

Reaction notes

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