Hydrochloric Acid → (E)-N-{(R)-1-aminomethyl-2-[4-(4-fluoro-phenoxy)-piperidin-1-yl]-ethyl}-3-(5-cyano-2-methoxy-phenyl)-acrylamide

HRID 1797272Notes

Reaction equation

HRID 1797272 reaction equation
C(OC(=O)[NH:7][CH2:8][C@@H:9]([NH:25][C:26](=[O:39])/[CH:27]=[CH:28]/[C:29]1[CH:34]=[C:33]([C:35]#[N:36])[CH:32]=[CH:31][C:30]=1[O:37][CH3:38])[CH2:10][N:11]1[CH2:16][CH2:15][CH:14]([O:17][C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[CH2:13][CH2:12]1)(C)(C)C.Cl>C(Cl)Cl.O1CCOCC1>[NH2:7][CH2:8][C@@H:9]([NH:25][C:26](=[O:39])/[CH:27]=[CH:28]/[C:29]1[CH:34]=[C:33]([C:35]#[N:36])[CH:32]=[CH:31][C:30]=1[O:37][CH3:38])[CH2:10][N:11]1[CH2:16][CH2:15][CH:14]([O:17][C:18]2[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=2)[CH2:13][CH2:12]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 68576228{(R)-2-[(E)-3-(5-cyano-2-methoxy-phenyl)-acryloylamino]-3-[4-(4-fluoro-phenoxy)-piperidin-1-yl]-propyl}-carbamic acid tert-butyl ester

Product 1

HCID 23566968(E)-N-{(R)-1-aminomethyl-2-[4-(4-fluoro-phenoxy)-piperidin-1-yl]-ethyl}-3-(5-cyano-2-methoxy-phenyl)-acrylamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of {(R)-2-[(E)-3-(5-cyano-2-methoxy-phenyl)-acryloylamino]-3-[4-(4-fluoro-phenoxy)-piperidin-1-yl]-propyl}-carbamic acid tert-butyl ester (0.39 g, 0.71 mmol) in DCM (2 ml) is treated with 4M hydrogen chloride in dioxane (1 ml). The reaction mixture is stirred at room temperature for 1.5 hours and then the solvent evaporated. The residue is co-evaporated with ethanol (×2) to afford (E)-N-{(R)-1-aminomethyl-2-[4-(4-fluoro-phenoxy)-piperidin-1-yl]-ethyl}-3-(5-cyano-2-methoxy-phenyl)-acrylamide.HCl salt. [MH]+ 453.2.

Workup

  1. customthe solvent evaporated

Sources & evidence

ORD record
ord-1f32b709f16b4d0fb0a816601871eb92
Source dataset
uspto-grants-2006_04
Patent number
US07034042B2

Reaction notes

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