Formaldehyde → HCID 69241284, compound

HRID 1295776Notes

Reaction equation

HRID 1295776 reaction equation
[C:1]1(C)C=CC(S(O)(=O)=O)=CC=1.[NH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[NH:19][CH:20]1[CH2:25][CH2:24][N:23]([C:26]([C:28]2[CH:33]=[CH:32][C:31]([CH2:34][CH2:35][CH2:36][CH3:37])=[CH:30][CH:29]=2)=[O:27])[CH2:22][CH2:21]1.C=O>C(#N)C>[N:19]1([CH:20]2[CH2:21][CH2:22][N:23]([C:26]([C:28]3[CH:33]=[CH:32][C:31]([CH2:34][CH2:35][CH2:36][CH3:37])=[CH:30][CH:29]=3)=[O:27])[CH2:24][CH2:25]2)[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]=[CH:1]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 6101p-Toluenesulfonic acidHCID 69240976HCID 69240976, compound

Product 1

HCID 69241284HCID 69241284, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

p-Toluenesulfonic acid (catalytic amount) was added to a solution of [4-(2-amino-phenylamino)-piperidin-1-yl]-(4-butyl-phenyl)-methanone (50 mg, 0.142 mmol) and paraformaldehyde (500 mg) in acetonitrile (10 mL). The reaction was heated at 80° C. for 4 h. The reaction mixture was concentrated and the crude product was purified by column chromatography on silica gel using chloroform/methanol/ammonia (96:3.6:0.4) as the eluent. The product fractions were combined and evaporated to give (4-benzoimidazol-1-yl-piperidin-1-yl)-(4-butyl-phenyl)-methanone (39 mg, 76%) as an amber oil.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe crude product was purified by column chromatography on silica gel
  3. customevaporated

Sources & evidence

ORD record
ord-213b6459380845e2ba8132c08740fe8a
Source dataset
uspto-grants-2007_07
Patent number
US07244744B2

Reaction notes

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