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Formaldehyde → 1-[4-(p-Fluorophenyl)-4-hydroxy-2-butynyl]-4-(2-keto-1-benzimidazolinyl)piperidine

HRID 596942
Notes
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Reaction equation

HRID 596942 reaction equation
[O:1]=[C:2]1[N:6]([CH:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[C:5]2[CH:13]=[CH:14][CH:15]=[CH:16][C:4]=2[NH:3]1.[CH2:17]=O.[F:19][C:20]1[CH:25]=[CH:24][C:23]([CH:26]([OH:29])[C:27]#[CH:28])=[CH:22][CH:21]=1>O1CCOCC1.O>[F:19][C:20]1[CH:21]=[CH:22][C:23]([CH:26]([OH:29])[C:27]#[C:28][CH2:17][N:10]2[CH2:9][CH2:8][CH:7]([N:6]3[C:5]4[CH:13]=[CH:14][CH:15]=[CH:16][C:4]=4[NH:3][C:2]3=[O:1])[CH2:12][CH2:11]2)=[CH:24][CH:25]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 886381,3-Dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-oneHCID 112751051-(4-Fluorophenyl)prop-2-yn-1-ol

Product 1

HCID 214494141-[4-(p-Fluorophenyl)-4-hydroxy-2-butynyl]-4-(2-keto-1-benzimidazolinyl)piperidine

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×
HCID 31275
1,4-Dioxane
Solvent
2×

Conditions

Temperature
80 °C

Procedure

To a solution of 4-(2-keto-1-benzimidazolinyl)piperidine (0.625 g) in a mixture of dioxane (10 ml), water (2 ml), and 37% formalin (0.40 g), there were added a solution of 3-(p-fluorophenyl)-3-hydroxy-1-propyne (0.45 g) in dioxane (2 ml) and a solution of cupric sulfate pentahydrate (30 mg) in water (1 ml) under ice-cooling. The resulting mixture was heated at 80° C for 4 hours and, after cooling, the resulting mixture was filtered and the filtrate was concentrated under reduced pressure and extracted with chloroform. The chloroform extracts were dried over magnesium sulfate. After evaporation of the solvent, the residual oil was chromatographed on silica gel to afford 1-[4-(p-fluorophenyl)-4-hydroxy-2-butynyl]-4-(2-keto-1-benzimidazolinyl)piperidine as oily substance. νOHneat or νNHneat 3200 cm-1, νC=Oneat 1680 cm-1.

Workup

  1. temperatureafter cooling
  2. filtrationthe resulting mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. extractionextracted with chloroform
  5. dry with materialThe chloroform extracts were dried over magnesium sulfate
  6. customAfter evaporation of the solvent
  7. customthe residual oil was chromatographed on silica gel

Sources & evidence

ORD record
ord-b7f0e022e6aa49e1977e81e5602bf973
Source dataset
uspto-grants-1977_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04012514

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes