Hydrochloric Acid → HCID 86755892, compound

HRID 365907Notes

Reaction equation

HRID 365907 reaction equation
[CH2:1]([C:4]1[CH:5]=[C:6]([O:11][CH2:12][C@@H:13]2[CH2:17][CH2:16][CH2:15][N:14]2[CH3:18])[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[CH2:17][CH2:16][CH2:15][N:14]2[CH3:18])[CH:7]=[N:8][C:9]=1[Cl:10])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 887MethanolHCID 54488670HCID 54488670, compound

Product 1

HCID 86755892HCID 86755892, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 5-allyl-6-chloro-3-(1-methyl-2-(S)-pyrrolidinylmethoxy)pyridine in Et2O was added hydrogen chloride (1.0 M in Et2O) carefully to afford the tittle compound: mp 150-152° C.; 1H NMR (D2O) δ 2.02-2.18 (m, 2H), 2.24 (m, 1H), 2.40 (m, 1H), 3.04 (s, 3H), 3.23 (m, 1H), 3.52 (d, 2H, J=6.5 Hz), 3.74 (m, 1H), 3.95 (m, 1H), 4.34 (dd, 1H, J=6.0, 11.5 Hz), 4.51 (dd, 1H, J=3.0, 11.0 Hz), 5.12 (dd, 1H, J=2.0, 17.5 Hz), 5.20 (dd, 1H, J=1.5, 10.0 Hz), 6.04 (m, 1H), 7.47 (d, 1H, J=3.0 Hz), 8.03 (d, 1H, J=3.0 Hz); MS (CI/NH3) m/z 267 (M+H)+. Anal. Calcd for C14H19ClN2O.1.1 HCl: C, 54.80; H, 6.60; N, 9.19. Found: C, 54.98; H, 6.37; N, 8.98. [α]25D -6.62 (c 1.5, MeOH).

Workup

  1. customto afford the tittle compound

Sources & evidence

ORD record
ord-9ec1f2e9b31f4ef38bb10ec8974e5fe6
Source dataset
uspto-grants-2000_10
Patent number
US06127386

Reaction notes

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