Hydrochloric Acid → HCID 9860821, compound

HRID 365881Notes

Reaction equation

HRID 365881 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([O:9][CH2:10][C@@H:11]2[CH2:15][CH2:14][CH2:13][N:12]2[CH3:16])[CH:6]=[N:7][CH:8]=1)=[CH2:2].[ClH:17].CO>CCOCC>[ClH:17].[ClH:17].[CH:1]([C:3]1[CH:4]=[C:5]([O:9][CH2:10][C@@H:11]2[CH2:15][CH2:14][CH2:13][N:12]2[CH3:16])[CH:6]=[N:7][CH:8]=1)=[CH2:2]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 887MethanolHCID 9860822HCID 9860822, compound

Product 1

HCID 9860821HCID 9860821, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 5-ethenyl-3-(1-methy-2-(S)-pyrrolidinyl-methoxy)pyridine from step b above in Et2O was added hydrogen chloride (1.0 M in Et2O) carefully to afford the tittle compound: mp 118-120° C.; 1H NMR (D2O) δ 2.56-2.76 (m, 3H), 3.00 (s, 3H), 4.03 (q, 1H, J=9.5 Hz), 4.29 (m, 1H), 4.52 (dd, 1H, J=5.5, 12.0 Hz), 4.60 (dd, 1H, J=3.0, 11.5 Hz), 5.65 (d, 1H, J=11.0 Hz), 6.09 (d, 1H, J=17.5 Hz), 6.84 (dd, 1H, J=11.0, 17.5 Hz), 8.02 (t, 1H, J=2.0 Hz), 8.36 (d, 1H, J=3.0 Hz), 8.43 (d, 1H, J=1.0 Hz); MS (CI/NH3) m/z 205 (N+H)+. Anal. Calcd for C12H16N2O.1.9 HCl: C, 50.69; H, 6.77; N, 9.85. Found: C, 50.79; H, 7.05; N, 9.48. [α]25D -20.43 (c 0.7, MeOH).

Workup

  1. customto afford the tittle compound

Sources & evidence

ORD record
ord-fa356cb6eccd48b18b17fac123eb7d46
Source dataset
uspto-grants-2000_10
Patent number
US06127386

Reaction notes

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