Hydrochloric Acid → HCID 22961887, compound

HRID 365899Notes

Reaction equation

HRID 365899 reaction equation
[CH2:1]([C:4]1[CH:5]=[C:6]([O:11][CH2:12][C@@H:13]2[CH2:16][CH2:15][N:14]2[CH3:17])[CH:7]=[N:8][C:9]=1[Cl:10])[CH:2]=[CH2:3].Cl.CO>CCOCC>[ClH:10].[CH2:1]([C:4]1[CH:5]=[C:6]([O:11][CH2:12][C@@H:13]2[CH2:16][CH2:15][N:14]2[CH3:17])[CH:7]=[N:8][C:9]=1[Cl:10])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 22961888HCID 22961888, compound

Product 1

HCID 22961887HCID 22961887, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 5-allyl-6-chloro-3-(1-methyl-2-(S)-azetidinylmethoxy)pyridine in Et2O was added hydrogen chloride (1.0 M in Et2O) carefully to afford the tittle compound: mp 109-111° C.; 1H NMR (D2O) δ 2.58-2.70 (m, 2H), 2.99 (s, 3H), 3.52 (d, 2H, J=6.5 Hz), 4.00 (m, 1H), 4.28 (m, 1H), 4.40-4.54 (m, 2H), 4.84 (m, 1H), 5.10-5.22 (m, 2H), 6.05 (m, 1H), 7.50 (d, 1H, J=3.0 Hz), 8.04 (d, 1H, J=3.0 Hz); MS (CI/NH3) m/z 254 (M+H)+. Anal. Calcd for C13H17ClN2O.HCl: C, 53.99; H, 6.27; N, 9.69. Found: C, 53.73; H, 6.01; N, 9.57. [α]25D -22.55 (c 2.2, MeOH).

Workup

  1. customto afford the tittle compound

Sources & evidence

ORD record
ord-ad02e266f3484c67bef38eb22990d757
Source dataset
uspto-grants-2000_10
Patent number
US06127386

Reaction notes

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