Propionic anhydride → HCID 178460016, compound

HRID 414235Notes

Reaction equation

HRID 414235 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([C:21]2[NH:25][N:24]=[N:23][N:22]=2)([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:26]([O:30][C:31](=[O:34])[CH2:32][CH3:33])(=[O:29])[CH2:27][CH3:28]>>[C:26]([O-:30])(=[O:29])[CH2:27][CH3:28].[CH2:1]([NH+:8]1[CH2:13][CH2:12][C:11]([C:21]2[NH:22][N:23]=[N:24][N:25]=2)([N:14]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:31](=[O:34])[CH2:32][CH3:33])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 31263Propionic anhydrideHCID 178420312HCID 178420312, compound

Product 1

HCID 178460016HCID 178460016, compound

Procedure

A 250 ml r.b. flask was charged with 1-benzyl-4-(1H-tetrazol-5-yl)-4-anilinopiperidine (17.7 g, 53 mmol) and propionic anhydride (95 ml). The resulting mixture was stirred at 70°-75° C. for 6 hours. Then, it was concentrated in vacuo and the crude was chromatographed (SiO2, 5-20% MeOH/CH2Cl2) to give the desired compound (14.7 g, 32 mmol) as white powder: m.p. 226°-228° C.; R (nujol) 1660 cm-1 ; MR (270 MHz, CDCl3) δ 0.864, (t, 3H, CH3CH2CON), 1.175 (t, 3H, CH3CH2CO2H), 1.883 (q, 2H, CH3CH2CO2H), 2.113 (m, 4H), 2.395 (q, 2H, CH3CH2CO2H), 2.8-3.1 (m, 4H), 3.464 (s, 2H, benzyl CH 2), 7.1 to 7.5 (complex, 10H, phenyl H's). Anal. Calcd. for C22H26N6O.C3H6O2 : C, 64.64; H, 6.94; N, 18.09. Found: C, 64.65; H, 7.00; N, 17.89. ##STR24##

Workup

  1. concentrationThen, it was concentrated in vacuo
  2. customthe crude was chromatographed (SiO2, 5-20% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-7244f3c92c2042baad684451afb78e09
Source dataset
uspto-grants-1988_12
Patent number
US04791120

Reaction notes

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