Hydrochloric Acid → HCID 67538760, compound

HRID 1192418Notes

Reaction equation

HRID 1192418 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][N:10]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=1)[C:11](=[O:24])[C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)=[CH:14][CH:13]=1)(C)(C)C.[ClH:34]>O1CCOCC1.C(OCC)C>[ClH:32].[ClH:34].[NH2:7][CH2:8][CH2:9][N:10]([CH2:25][C:26]1[CH:27]=[CH:28][C:29]([Cl:32])=[CH:30][CH:31]=1)[C:11](=[O:24])[C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:19]=[CH:20][N:21]=[CH:22][CH:23]=2)=[CH:14][CH:13]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67540133HCID 67540133, compound

Product 1

HCID 67538760HCID 67538760, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent2×

Procedure

The {2-[(4-chlorobenzyl)-(4-pyridin-4-yl-benzoyl)-amino]-ethyl}-carbamic acid tert-butyl ester (184 mg, 0.395 mmol) was dissolved in 2.0 mL of 1,4-dioxane and treated with 2.0 mL of 4M HCl in 1,4-dioxane. The reaction was allowed to stir for one hour to completion and diluted with diethyl ether. The product was isolated by vacuum filtration to afford the N-(2-amino-ethyl)-N-(4-chlorobenzyl)-4-pyridin-4-yl-benzamide bis-hydrochloride salt as a fine pale-yellow powder (166 mg, 96%). 1H NMR (DMSO-d6, 400 MHz) δ 8.91 (d, J=6.0 Hz, 2H), 8.26 (d, J=6.0 Hz, 2H), 8.13 (brs, 3H), 8.05 (d, J=8.0 Hz, 2H), 7.76 (d, J=7.6 Hz, 2H), 7.45 (brs, 1H), 7.44 (d, J=8.0 Hz, 2H), 7.26 (d, J=7.6 Hz, 2H), 4.57 (brs, 2H), 3.61 (m, 2H), 3.08 (m, 2H). LCMS (APCI+) m/z 366 [M+H]+; Rt=2.13 min.

Workup

  1. customThe product was isolated by vacuum filtration

Sources & evidence

ORD record
ord-208accbe098a4216a562ae315d3065ed
Source dataset
uspto-grants-2014_03
Patent number
US08680114B2

Reaction notes

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