Propionamide → HCID 13345109, compound

HRID 1462018Notes

Reaction equation

HRID 1462018 reaction equation
C(N)(=O)CC.[CH2:6]1[O:14][C:13]2[CH:12]=[CH:11][C:10]([NH:15][C:16](=O)[CH:17]([N:19]3[CH2:24][CH2:23][N:22]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=4)[CH2:21][CH2:20]3)[CH3:18])=[CH:9][C:8]=2[O:7]1>C1COCC1>[N:26]1[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=1[N:22]1[CH2:23][CH2:24][N:19]([CH:17]([CH3:18])[CH2:16][NH:15][C:10]2[CH:11]=[CH:12][C:13]3[O:14][CH2:6][O:7][C:8]=3[CH:9]=2)[CH2:20][CH2:21]1

Participants

4

Reactant 2

HCID 6578PropionamideHCID 4883264HCID 4883264, compound

Product 1

HCID 13345109HCID 13345109, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The propionamide prepared according to part (b) is finally reduced with AlLiH4 in THF by the conventional method. The crude reaction product in the form of a dense oil is purified by column chromatography, (petroleum ether-ethyl acetate-triethylamine, 80:10:10), thus obtaining the desired product (22). The melting point is 91°-92° C.; Rf 0.19 (petroleum ether-ethyl acetate Et3N 8:1:1), IR (nujol) νmax: 3340, 3310, 1595, 1500, 1480, 1440, 1315, 1250, 1235, 1210, 1170, 1050, 930, 780 cm-1. 1H-NMR (CDCl3): 1.03 (d, J=5 Hz; 3H); 2.20-3.13 (m; 7H); 3.30-3.63 (m; 4H); 4.13 (s broadened; 1H); 5.77 (s, 2H); 5.97 (doublet d, J1 =8 Hz, J2 =2 Hz; 1H); 6.20 (d, J=2 Hz; 1H); 6.33-6.70 (m; 3H); 7.13-7.55 (m; 1H); 8.00-8.20 (m; 1H).

Workup

  1. customThe crude reaction product in the form of a dense oil
  2. customis purified by column chromatography, (petroleum ether-ethyl acetate-triethylamine, 80:10:10),

Sources & evidence

ORD record
ord-467a9cffcdbe48d0ab53a02b31c2b243
Source dataset
uspto-grants-1984_07
Patent number
US04457931

Reaction notes

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