Acetyl chloride → 4-[3-(4-Methanesulfonyl-benzyl)-[1,2,4]oxadiazol-5-yl]-piperidine hydrochloride

HRID 1593001Notes

Reaction equation

HRID 1593001 reaction equation
C([Cl:4])(=O)C.[CH3:5][S:6]([C:9]1[CH:33]=[CH:32][C:12]([CH2:13][C:14]2[N:18]=[C:17]([CH:19]3[CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21][CH2:20]3)[O:16][N:15]=2)=[CH:11][CH:10]=1)(=[O:8])=[O:7]>CO>[ClH:4].[CH3:5][S:6]([C:9]1[CH:10]=[CH:11][C:12]([CH2:13][C:14]2[N:18]=[C:17]([CH:19]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)[O:16][N:15]=2)=[CH:32][CH:33]=1)(=[O:7])=[O:8]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 68709899Tert-butyl 4-{3-[4-(methylsulfonyl)benzyl]-1,2,4-oxadiazol-5-yl}piperidine-1-carboxylate

Product 1

HCID 694496664-[3-(4-Methanesulfonyl-benzyl)-[1,2,4]oxadiazol-5-yl]-piperidine hydrochlorideYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A premixed solution of acetyl chloride (0.97 mL, 11.86 mmol) was added dropwise to methanol (10 mL), stirred for 10 minutes and tert-butyl 4-{3-[4-(methylsulfonyl)benzyl]-1,2,4-oxadiazol-5-yl}piperidine-1-carboxylate (2.50 g, 5.93 mmol) was added and the mixture heated to reflux for 2 hours. The solvents were evaporated and the residue triturated with diethyl ether, filtered and dried to give the title compound as a fine white powder (2.05 g, 97%); NMR 1.97 (2H, m), 2.17(2H, dd), 3.02(2H, m), 3.31 (2H, m), 3.41 (1H, m), 4.25 (2H, s), 7.59 (2H, d), 7.89 (2H, d), 9.27(1H, br s), 9.35 (1H, br s); MS: 322 (MH+).

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux for 2 hours
  3. customThe solvents were evaporated
  4. customthe residue triturated with diethyl ether
  5. filtrationfiltered
  6. customdried

Sources & evidence

ORD record
ord-982c3ce5f6ff414097296deccbba5bf8
Source dataset
uspto-grants-2007_11
Patent number
US07294636B2

Reaction notes

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