Hydrochloric Acid → Benzyl 4-(4-(2-imino-2-methoxyethyl)pyridin-2-yl)piperazine-1-carboxylate

HRID 517562Notes

Reaction equation

HRID 517562 reaction equation
Cl.[C:2]([CH2:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([N:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:18])[CH2:13][CH2:12]2)[CH:6]=1)#[N:3].[CH3:27][OH:28]>>[NH:3]=[C:2]([O:28][CH3:27])[CH2:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([N:11]2[CH2:12][CH2:13][N:14]([C:17]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:18])[CH2:15][CH2:16]2)[CH:6]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 86711501Benzyl 4-(4-(cyanomethyl)pyridin-2-yl)piperazine-1-carboxylate

Product 1

HCID 86711502Benzyl 4-(4-(2-imino-2-methoxyethyl)pyridin-2-yl)piperazine-1-carboxylate

Procedure

Hydrochloric acid gas was bubbled into a stirred solution of benzyl 4-(4-(cyanomethyl)pyridin-2-yl)piperazine-1-carboxylate (500 mg, 1.5 mmol) in dry MeOH (10 mL) for 5 h at 0° C., and then concentrated at 10° C. to give the crude product, which was used directly for the next step. MS (ES+) C20H24N4O3 requires: 368, found: 369 [M+H]+.

Workup

  1. concentrationconcentrated at 10° C.

Sources & evidence

ORD record
ord-d7a03b551e0c489ca7e2e17a3b7b0ea2
Source dataset
uspto-grants-2015_08
Patent number
US09115120B2

Reaction notes

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