Hydrochloride methanol → 4-(4-Aminobutyl)-N-(2-hydroxyethyl)benzamide hydrochloride

HRID 81335Notes

Reaction equation

C(OC(=O)[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18](=[O:23])[NH:19][CH2:20][CH2:21][OH:22])=[CH:14][CH:13]=1)(C)(C)C.CO.[ClH:27]>>[ClH:27].[NH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]([NH:19][CH2:20][CH2:21][OH:22])=[O:23])=[CH:14][CH:13]=1

Participants

Reactant 2

HCID 21893726Hydrochloride methanol

HCID 67366053HCID 67366053, compound

Product 1

HCID 673681504-(4-Aminobutyl)-N-(2-hydroxyethyl)benzamide hydrochlorideYield 98%

Procedure

A solution of 27 (0.4 g, 1.19 mmol) was stirred at room temperature in a mixture of methanol/HCl (1:1, 40 mL). The reaction was finished in 2 h according to HPLC analysis. The solvent was removed under reduced pressure to provide 0.33 g (98%) 28 as a white solid. 1H NMR (300 MHz, DMSO-d6) δ 1.60 (m, 4H), 2.63 (m, 2H), 2.78 (m, 2H), 3.31 (m, 2H), 3.50 (m, 2H), 7.28 (d, 2H), 7.80 (d, 2H), 7.97 (br s, 2H), 8.46 (m, 1H).

Workup

customThe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-a37f9ddf9d5047bba8675f6f1bf04809
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846688B2

Reaction notes

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