Acetyl chloride → 4-(3-Methyl-1,2,4-oxadiazol-5-yl)piperidine hydrochloride

HRID 1593006Notes

Reaction equation

HRID 1593006 reaction equation
[CH3:1][C:2]1[N:6]=[C:5]([CH:7]2[CH2:12][CH2:11][N:10](C(OC(C)(C)C)=O)[CH2:9][CH2:8]2)[O:4][N:3]=1.C([Cl:23])(=O)C>CO>[ClH:23].[CH3:1][C:2]1[N:6]=[C:5]([CH:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[O:4][N:3]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 210983601,1-Dimethylethyl 4-(3-methyl-1,2,4-oxadiazol-5-yl)-1-piperidinecarboxylate

Product 1

HCID 457918884-(3-Methyl-1,2,4-oxadiazol-5-yl)piperidine hydrochlorideYield 55%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
60 °C

Procedure

Crude tert-butyl 4-(3-methyl-1,2,4-oxadiazol-5-yl)piperidine-1-carboxylate (5.73 g, 21.3 mmol) was dissolved in MeOH (100 mL) and a premixed solution of acetyl chloride (1.53 mL, 42.8 mmol) in MeOH (10 mL) was added and the mixture heated to 60° C. for 1 hour, then the solvents were evaporated and the resultant gum triturated with dichloromethane/diethyl ether (1:1) to give a cream solid which was filtered, washed with diethyl ether and dried, to give the title compound as a solid (1.98 g, 55% yield); MS: 168 (MH+).

Workup

  1. customthe solvents were evaporated
  2. customthe resultant gum triturated with dichloromethane/diethyl ether (1:1)
  3. customto give a cream solid which
  4. filtrationwas filtered
  5. washwashed with diethyl ether
  6. customdried

Sources & evidence

ORD record
ord-b51cf27fcf4f48e2be4bf1cc431a7188
Source dataset
uspto-grants-2007_11
Patent number
US07294636B2

Reaction notes

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