Hydrochloric Acid → [1-(3-Methyl-1,2,4-oxadiazol-5-yl)-4-piperidinyl]methanol

HRID 423478Notes

Reaction equation

HRID 423478 reaction equation
CCOCC.[OH:6][CH2:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14]#[N:15])[CH2:10][CH2:9]1.[OH:16][NH:17][C:18](=N)[CH3:19].Cl>CCOC(C)=O.CCO.[Cl-].[Cl-].[Zn+2]>[CH3:19][C:18]1[N:15]=[C:14]([N:11]2[CH2:12][CH2:13][CH:8]([CH2:7][OH:6])[CH2:9][CH2:10]2)[O:16][N:17]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 513582894-(Hydroxymethyl)piperidine-1-carbonitrileHCID 178465666HCID 178465666, compound

Product 1

HCID 59177773[1-(3-Methyl-1,2,4-oxadiazol-5-yl)-4-piperidinyl]methanolYield 13%

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

[1-(3-Methyl-1,2,4-oxadiazol-5-yl)-4-piperidinyl]methanol (143 mg, 13%) was prepared from a solution of 1N ZnCl2 in Et2O (6.8 mL, 6.8 mmol), 4-(hydroxymethyl)-1-piperidinecarbonitrile (prepared as in Example 20, Step 1, 0.79 g, 5.6 mmol) and N-hydroxyacetamidine (0.5 g, 6.8 mmol) in EtOAc (10 mL) followed by concentrated HCl (2 mL) in EtOH (2 mL) in a manner similar to Example 20, Step 3. 1H NMR (400 MHz, CDCl3): δ 4.22-4.10 (m, 2H), 3.54 (d, 2H, J=6.4 Hz), 3.11-3.01 (m, 2 H), 2.21 (s, 3H), 1.89-1.79 (m, 2H), 1.78-1.69 (m, 1H), 1.41-1.20 (m, 2H); LRMS (ESI), m/z 198 (M+H).

Sources & evidence

ORD record
ord-80430343ebff492ca1e8710dabe71b5d
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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