Hydrochloric Acid → HCID 54100857, compound

HRID 2305170Notes

Reaction equation

HRID 2305170 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([O:8][CH2:9][C@H:10]2[CH2:14][CH2:13][CH2:12][NH:11]2)=[CH:4][C:3]=1[CH:15]=[CH2:16].Cl.[CH3:18]O>CCOCC>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([O:8][CH2:9][C@H:10]2[CH2:14][CH2:13][CH2:12][N:11]2[CH3:18])=[CH:4][C:3]=1[CH:15]=[CH2:16]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 887MethanolHCID 53692945HCID 53692945, compound

Product 1

HCID 54100857HCID 54100857, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 6-chloro-5-ethenyl-3-(2-(R)-pyrrolidinylmethoxy)pyridine in Et2O was added hydrogen chloride (1.0 M in Et2O) carefully to afford the tittle compound: mp 173-175° C.; 1H NMR (D2O) δ 2.04-2.18 (m, 2H), 2.23 (m, 1H), 2.40 (m, 1H), 3.04 (s, 3H), 3.29 (m, 1H), 3.73 (m, 1H), 3.95 (m, 1H), 4.37 (dd, 1, J=6.0, 11.0 Hz), 4.53 (dd, 1H, J=3.0, 11.0 Hz), 5.61 (d, 1H, J=11.0 Hz), 5.94 (d, 1H, J=17.5 Hz), 7.02 (dd, 1H, J=11.0, 17.5 Hz), 7.73 (d, 1H, J=3.0 Hz), 8.04 (d, 1H, J=3.0 Hz); MS (CI/NH3) m/z 253 (M+H)+. Anal. Calcd for C13H17ClN2O.1.1 HCl: C, 53.32; H, 6.23; N, 9.57. Found: C, 53.51; H, 6.48; N, 9.20. [α]25D +7.4 (c 0.66 MeOH).

Workup

  1. customto afford the tittle compound

Sources & evidence

ORD record
ord-6017cbf458734fd89207545b05583935
Source dataset
uspto-grants-2002_08
Patent number
US06437138B1

Reaction notes

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