Hydrochloric Acid → HCID 69830778, compound

HRID 365896Notes

Reaction equation

HRID 365896 reaction equation
[CH2:1]([C:4]1[CH:5]=[C:6]([O:10][CH2:11][C@@H:12]2[CH2:16][CH2:15][CH2:14][N:13]2[CH3:17])[CH:7]=[N:8][CH:9]=1)[CH:2]=[CH2:3].[ClH:18].Cl.O.CO>CCOCC>[ClH:18].[ClH:18].[CH2:1]([C:4]1[CH:5]=[C:6]([O:10][CH2:11][C@@H:12]2[CH2:16][CH2:15][CH2:14][N:13]2[CH3:17])[CH:7]=[N:8][CH:9]=1)[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 21885828Hydrate;hydrochlorideHCID 22961889HCID 22961889, compound

Product 1

HCID 69830778HCID 69830778, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 5-allyl-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 65-67° C.; 1H NMR (D2O) δ 2.00-2.17 (m, 2H), 2.23 (m, 1H), 2.41 (m, 1H), 3.05 (s, 3H), 3.27 (m, 1H), 3.56 (dd, 2H, J=3.5, 7.0 Hz), 3.77 (m, 1H), 3.95 (m, 1H), 4.44 (dd, 1H, J=6.0, 11.0 Hz), 4.60 (dd, 1H, J=3.0, 11.0 Hz), 5.18-5.24 (m, 2H), 6.04 (m, 1H), 7.88 (s, 1H), 8.28 (s, 1H), 8.35 (s, 1H); MS (CI/NH3) m/z 232 (M+H)+. Anal. Calcd for C14H20N2O.2 HCl.H2O: C, 52.02; H, 7.48; N, 8.67. Found: C, 52.15; H, 7.42; N, 8.72. [α]25D -4.77 (c 2.41, MeOH).

Workup

  1. customto afford the tittle compound

Sources & evidence

ORD record
ord-43e90f92c8904aa4b66bd8558a2457fe
Source dataset
uspto-grants-2000_10
Patent number
US06127386

Reaction notes

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