2-Hydroxyisobutyric acid → HCID 58852276, compound

HRID 1716568Notes

Reaction equation

HRID 1716568 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][C:16]=2[NH2:22])[CH2:10][CH2:9]1)=O)(C)(C)C.[OH:23][C:24]([CH3:29])([CH3:28])[C:25](O)=O>>[CH3:21][C:18]1[CH:19]=[CH:20][C:15]2[N:14]([CH:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)[C:25]([C:24]([OH:23])([CH3:29])[CH3:28])=[N:22][C:16]=2[CH:17]=1

Participants

3

Reactant 2

HCID 116712-Hydroxyisobutyric acidHCID 588522881,1-Dimethylethyl 4-[(2-amino-4-methylphenyl)amino]-1-piperidinecarboxylate

Product 1

HCID 58852276HCID 58852276, compound

Procedure

2-(5-Methyl-1-piperidin-4-yl-1H-benzoimidazol-2-yl)-propan-2-ol was prepared from 4-(2-amino-4-methyl-phenylamino)-piperidine-1-carboxylic acid tert-butyl ester and 2-hydroxyisobutyric acid according to the procedure described by Skolnik et. al. J. Amer. Chem. Soc., 1943, 65, 1854-1858. The yields of the product after washing with water and drying varied from 78-87% as an off-white solid. 1H NMR (DMSO-d6, 300 MHz) δ 7.60, 7.36, 6.99, 5.63 (s, 1H), 5.30 (m, 1H), 3.10 (br m, 2H), 2.54 (br m, 2H), 2.37 (s, 3H), 2.22-2.36 (m, 3H), 1.74 (brd, 2H), 1.61 (s, 6H).

Workup

  1. customThe yields of the product
  2. washafter washing with water
  3. customdrying

Sources & evidence

ORD record
ord-f4351d8d0dd449f09f0ed594079937f2
Source dataset
uspto-grants-2010_09
Patent number
US07803816B2

Reaction notes

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