Hydrochloric Acid → 2-[4-(4-Aminobutyl)phenylamino]acetamide

HRID 254375Notes

Reaction equation

HRID 254375 reaction equation
Cl.C(OC(=O)[NH:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([NH:19][CH2:20][C:21](=[O:23])[NH2:22])=[CH:15][CH:14]=1)(C)(C)C>>[NH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([NH:19][CH2:20][C:21]([NH2:22])=[O:23])=[CH:15][CH:14]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 58664816{4-[4-(Carbamoylmethylamino)phenyl]butyl}carbamic acid tert-butyl ester

Product 1

HCID 586648462-[4-(4-Aminobutyl)phenylamino]acetamideYield 72.9%

Procedure

12N HCl (5 mL) was added to {4-[4-(carbamoylmethylamino)phenyl]butyl}carbamic acid tert-butyl ester 390 (0.2 g, 0.62 mmol). The reaction was stirred at room temperature for 1 hour. The solvent was evaporated in vacuo. The residue was purified by flash chromatography (silica gel, 4:1:0.1 chloroform/methanol/concentrated ammonium hydroxide, v/v) to provide 400 (0.10 g, 70%) as a white solid. 1H NMR (300 MHz, CD3OD) δ 1.55 (m, 4H), 2.50 (t, 2H), 2.68 (t, 2H), 3.70 (s, 2H), 6.52 (d, 2H), 6.97 (d, 2H).

Workup

  1. customThe solvent was evaporated in vacuo
  2. customThe residue was purified by flash chromatography (silica gel, 4:1:0.1 chloroform/methanol/concentrated ammonium hydroxide, v/v)

Sources & evidence

ORD record
ord-1f136dbe774a48ab96251025a79ae6dc
Source dataset
uspto-grants-2011_01
Patent number
US07875619B2

Reaction notes

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