Hydrochloric Acid → 3-(3-Methyl-1,2,4-oxadiazol-5-yl)piperidine

HRID 532970Notes

Reaction equation

HRID 532970 reaction equation
[CH3:1][C:2]1[N:6]=[C:5]([CH:7]2[CH2:12][CH2:11][CH2:10][N:9](C(OC(C)(C)C)=O)[CH2:8]2)[O:4][N:3]=1.Cl.C(O)C.CC(OC)(C)C>ClCCl>[CH3:1][C:2]1[N:6]=[C:5]([CH:7]2[CH2:12][CH2:11][CH2:10][NH:9][CH2:8]2)[O:4][N:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 15413tert-Butyl methyl etherHCID 58487582HCID 58487582, compound

Product 1

HCID 64866033-(3-Methyl-1,2,4-oxadiazol-5-yl)piperidineYield 114.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

tert-Butyl 3-(3-methyl-1,2,4-oxadiazol-5-yl)piperidine-1-carboxylate 2a,b (0.81 g, 0.0030 mol) was dissolved in 5 mL dichloromethane. Hydrochloric acid in ethanol (2.5 M) (2.43 mL, 0.0060 mol) was added and the mixture was heated to 40° C. for 3 hours. 20 mL of MTBE was added and the product precipitated from solution. The solids were filtered and washed with 3×5 mL MTBE and dried under vacuum overnight to obtain 574 mg of a white solid in 94% yield. MS (ESI) m/z 168 [M+1]+. 1H NMR (DMSO-d6) δ 1.74-1.82 (m, 3H), 2.11-2.14 (d, 1H), 2.31 (s, 3H), 2.87 (t, 1H), 3.10-3.30 (m, 2H), 3.49-3.56 (m, 3H).

Workup

  1. customthe product precipitated from solution
  2. filtrationThe solids were filtered
  3. washwashed with 3×5 mL MTBE
  4. customdried under vacuum overnight

Sources & evidence

ORD record
ord-af284246ec5f411793a675b2976d2eef
Source dataset
uspto-grants-2014_10
Patent number
US08853219B2

Reaction notes

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