Hydrochloric Acid → HCID 86755889, compound

HRID 365880Notes

Reaction equation

HRID 365880 reaction equation
[CH3:1][C:2]([CH3:21])([CH3:20])[CH:3]=[CH:4][CH:5]=[CH:6][C:7]1[CH:8]=[C:9]([O:13][CH2:14][C@@H:15]2[CH2:19][CH2:18][CH2:17][NH:16]2)[CH:10]=[N:11][CH:12]=1.[ClH:22].CO>CCOCC>[ClH:22].[ClH:22].[NH:16]1[CH2:17][CH2:18][CH2:19][C@H:15]1[CH2:14][O:13][C:9]1[CH:10]=[N:11][CH:12]=[C:7]([CH:6]=[CH:5][CH:4]=[CH:3][C:2]([CH3:21])([CH3:20])[CH3:1])[CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 887MethanolHCID 54102698HCID 54102698, compound

Product 1

HCID 86755889HCID 86755889, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 5-(5,5-dimethyl-hexadienyl)-3-(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 92-94° C.; 1H NMR (D2O) δ 1.95 (m, 1H), 2.04-2.20 (m, 2H), 2.30 (m, 1H), 3.43 (t, 2H, J=7.0 Hz), 4.17 (m, 1H), 4.38 (dd, 1H, J=7.5, 11.0 Hz), 4.59 (dd, 1H, J=3.5, 10.5 Hz), 6.23 (d, 1H, J=15.5 Hz), 6.35 (dd, 1H, J=10.0, 15.5 Hz), 6.58 (d, 1H, J=16.0 Hz), 7.14 (dd, 1H, J=16.0 Hz), 8.06 (t, 1H, J=2.5 Hz), 8.28 (d, 1H, J=2.5 Hz), 8.41 (s, 1H); MS (CI/NH3) m/z 287 (M+H)+. Anal. Calcd for C18H26N2O.2.7 HCl: C, 56.18; H, 7.52; N, 7.28. Found: C, 56.12; H, 7.47; N, 7.14. [α]25D +6.98 (c 0.94, MeOH).

Workup

  1. customto afford the tittle compound

Sources & evidence

ORD record
ord-56ae2c74c93b44d0a7ecd7e295b1e332
Source dataset
uspto-grants-2000_10
Patent number
US06127386

Reaction notes

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