Dichloromethane → HCID 69948166, compound

HRID 397646Notes

Reaction equation

[CH2:1]([C:8]1[O:12][N:11]=[C:10]([C@@H:13]2[CH2:18][CH2:17][CH2:16][CH2:15][N:14]2C(OC(C)(C)C)=O)[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:26]CCl>>[ClH:26].[CH2:1]([C:8]1[O:12][N:11]=[C:10]([C@@H:13]2[CH2:18][CH2:17][CH2:16][CH2:15][NH:14]2)[N:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Reactant 2

HCID 6344Dichloromethane

HCID 57092040HCID 57092040, compound

Product 1

HCID 69948166HCID 69948166, compound

Conditions

Temperature: 0 °C

Procedure

tert-Butyl (2S)-2-(5-benzyl-1,2,4-oxadiazol-3-yl)-1-piperidinecarboxylate (10.59 g) [see Preparation 6] was dissolved in dichloromethane (150 ml) and cooled to 0° C. Hydrogen chloride gas was then bubbled through until the point of saturation. The reaction mixture was then stirred for 30 mins. at 0° C., the solvent was removed under reduced pressure and the product azeotroped with dichloromethane to afford 5-benzyl-3-[(2S)-2-piperidyl]-1,2,4-oxadiazole hydrochloride (8.3 g) as a yellow solid.

Workup

customHydrogen chloride gas was then bubbled through until the point of saturation
customat 0° C., the solvent was removed under reduced pressure
customthe product azeotroped with dichloromethane

Sources & evidence

ORD record: ord-e6d3c1729f6e4867b1d9c9fc22e0242c
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06610707B1

Reaction notes

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