Ethyl 4-bromobutyrate → Ethyl 4-[(3-hydroxypropyl)phenylamino]butanoate

HRID 47963

Reaction equation

[C:1]1([NH:7][CH2:8][CH2:9][CH2:10][OH:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17]>C(N(C(C)C)C(C)C)C>[OH:11][CH2:10][CH2:9][CH2:8][N:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 3-(phenylamino)propan-1-ol (Huang, Yande; Arif, Atta M.; Bentrude, Weseley G. J. Org. Chem.; 58; 23; 1993; 6235-6246) (65.6 g, 0.43 mol), ethyl 4-bromobutyrate (104.5 g, 0.54 mol) and 100 mL of ethyldiisopropylamine is stirred at 100° C. for 1 h. The reaction is cooled to room temperature and partitioned between water 400 mL and ethyl acetate (500 mL). The organic layer is washed with saturated NaHCO3, brine and dried over Na2SO4. The oil obtained after concentration is chromatographed on silica eluting with 10% EtOH/CHCl3. Concentration of the appropriate fractions affords 115 g (100%) of the desired product as a colorless, viscous oil. 1H NMR (CDCl3) δ: 7.23 (m, 2H), 6.72 (m, 3H), 4.14 (q, J=7 Hz, 2H), 3.72 (t, J=6 Hz, 2H), 3.43 (t, 7 Hz, 2H), 3.34 (t, 7 Hz, 2H), 2.35 (t, 7 Hz), 1.88 (m, 4H), 1.26 (t, 7 Hz, 3H).

Workup

temperatureThe reaction is cooled to room temperature
custompartitioned between water 400 mL and ethyl acetate (500 mL)
washThe organic layer is washed with saturated NaHCO3, brine
dry with materialdried over Na2SO4
customThe oil obtained
concentrationafter concentration
customis chromatographed on silica eluting with 10% EtOH/CHCl3

Sources & evidence

ORD record: ord-da4a2ab280e140678541c3e0bbe679eb
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06699975B2

Linked notes

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