{4-[4-(3-Carbamoylpropylamino)phenyl]butyl}carbamic acid tert-butyl ester → 4-[4-(4-Aminobutyl)phenylamino]butyramide

HRID 254378Notes

Reaction equation

HRID 254378 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][CH2:19][CH2:20][CH2:21][C:22](=[O:24])[NH2:23])=[CH:14][CH:13]=1)(C)(C)C>C(O)(C(F)(F)F)=O.ClCCl>[NH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][CH2:19][CH2:20][CH2:21][C:22]([NH2:23])=[O:24])=[CH:14][CH:13]=1

Participants

3

Reactant 1

HCID 58664823{4-[4-(3-Carbamoylpropylamino)phenyl]butyl}carbamic acid tert-butyl ester

Product 1

HCID 586648354-[4-(4-Aminobutyl)phenylamino]butyramide

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

{4-[4-(3-Carbamoylpropylamino)phenyl]butyl}carbamic acid tert-butyl ester 430 (0.23 g, 0.66 mmol) was cooled to 0° C. in an ice bath. A cold solution of TFA/dichloromethane (10 mL) was added. The reaction was slowly warmed to room temperature and stirred for 30 minutes. The solvent was evaporated in vacuo to provide 440. 1H NMR (300 MHz, CD3OD) δ 1.69 (m, 4H), 1.95 (m, 2H), 2.47 (m, 2H), 2.71 (m, 2H), 2.93 (m, 2H), 3.39 (m, 2H), 7.39 (s, 4H). m/z (ESI) 250.

Workup

  1. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-06f20629399a42e6b57a46d70182a8f2
Source dataset
uspto-grants-2011_01
Patent number
US07875619B2

Reaction notes

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