Hydrochloric Acid → HCID 69830758, compound

HRID 365877Notes

Reaction equation

HRID 365877 reaction equation
[C:1]([C:9]1[CH:10]=[C:11]([O:15][CH2:16][C@@H:17]2[CH2:21][CH2:20][CH2:19][NH:18]2)[CH:12]=[N:13][CH:14]=1)#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[ClH:22].CO>CCOCC>[ClH:22].[ClH:22].[C:1]([C:9]1[CH:10]=[C:11]([O:15][CH2:16][C@@H:17]2[CH2:21][CH2:20][CH2:19][NH:18]2)[CH:12]=[N:13][CH:14]=1)#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 887MethanolHCID 69830326HCID 69830326, compound

Product 1

HCID 69830758HCID 69830758, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 5-octynyl-3-(2-(S)-pyrrolidinylmethoxy)pyridine from step b above in Et2O was added hydrogen chloride (1.0 M in Et2O) carefully to afford the tittle compound: 1H NMR (D2O) δ0.87 (t, 3H, J=7.0 Hz), 1.32 (t, 4H, J=4.0 Hz), 1.45 (t, 2H, J=7.0 Hz), 1.96 (m, 1H), 2.02-2.20 (m, 2H), 2.29 (m, 1H), 2.49 (t, 2H, J=7.0 Hz), 3.41 (t, 2H, J=7.0 Hz), 4.14 (m, 1H), 4.33 (dd, 1H, J=7.5, 11.0 Hz), 4.54 (dd, 1H, J=3.5, 11.0 Hz), 7.90 (t, 1H, J=1.5 Hz), 8.37 (t, 2H, J=3.0 Hz); MS (CI/NH3) m/z 287 (M+H)+. Anal. Calcd for C18H26N2O·1.7 HCl: C, 62.06; H, 8.01; N, 8.04. Found: C, 62.03; H, 7.99; N, 7.74. [α]25D+7.0 (c 0.88, MeOH).

Workup

  1. customto afford the tittle compound

Sources & evidence

ORD record
ord-c4440a481d74457cb755a17fdf6471a2
Source dataset
uspto-grants-2000_10
Patent number
US06127386

Reaction notes

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