Hydrochloric Acid → HCID 9795974, compound

HRID 365906Notes

Reaction equation

HRID 365906 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][NH:14]2)[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][NH:14]2)[CH:7]=[N:8][C:9]=1[Cl:10])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 887MethanolHCID 9795975HCID 9795975, compound

Product 1

HCID 9795974HCID 9795974, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 5-allyl-6-chloro-3-(2-(S)-pyrrolidinylmethoxy)pyridine in Et2O was added hydrogen chloride (1.0 M in Et2O) carefully to afford the tittle compound: 1H NMR (D2O) δ 1.94 (m, 1H), 2.04-2.22 (m, 2H), 2.30 (m, 1H), 3.42 (t, 2H, J=7 Hz), 3.51 (d, 2H, J=7.0 Hz), 4.10 (m, 1H), 4.23 (dd, 1H, J=7.5, 10.5 Hz), 4.45 (dd, 1H, J=3.5, 11.0 Hz), 5.06-5.20 (m, 2H), 6.04 (m, 1H), 7.45 (d, 1H, J=3.0 Hz), 7.99 (d, 1H, J=3.0 Hz); MS (CI/NH3) m/z 353 (M+H)+. Anal. Calcd for C13H17ClN2O.1.4 HCl: C, 51.40; H, 6.10; N, 9.22. Found: C, 51.71; H, 5.92; N, 8.89. [α]25D +16.70 (c 21.5, MeOH).

Workup

  1. customto afford the tittle compound

Sources & evidence

ORD record
ord-feff38abccf74b68b7374050dba28b4e
Source dataset
uspto-grants-2000_10
Patent number
US06127386

Reaction notes

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