Furfuryl Alcohol → 4-(1-(fur-2-ylmethyl)-1H-benzimidazole-2-carbonyl)piperidine

HRID 609781Notes

Reaction equation

HRID 609781 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([C:16]2[NH:20][C:19]3[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=3[N:17]=2)=[O:15])[CH2:10][CH2:9]1)=O)(C)(C)C.[CH2:25](O)[C:26]1[O:30][CH:29]=[CH:28][CH:27]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[O:30]1[CH:29]=[CH:28][CH:27]=[C:26]1[CH2:25][N:20]1[C:19]2[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=2[N:17]=[C:16]1[C:14]([CH:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1)=[O:15]

Participants

6

Reactant 4

HCID 7361Furfuryl AlcoholHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 183332351-(t-butoxycarbonyl)-4-(1H-benzimidazole-2-carbonyl)piperidine

Product 1

HCID 183335194-(1-(fur-2-ylmethyl)-1H-benzimidazole-2-carbonyl)piperidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Combine 1-(t-butoxycarbonyl)-4-(1H-benzimidazole-2-carbonyl)piperidine (1.16 mmol), furfuryl alcohol (0.10 mL, 1.16 mmol), and triphenylphosphine (0.33 g, 1.28 mmol) in tetrahydrofuran (5 mL). Add diethyl azodicarboxylate (0.20 mL, 1.28 mmol). After 18 hours, evaporate the reaction mixture in vacuo to give a residue. Partition the residue between ethyl acetate and water. Separate the organic layer and extract with water and saturated aqueous sodium chloride solution. Dry the organic layer over Na2SO4, filter, and evaporate invacuo to give the title compound. Chromatograph the residue on silica gel eluting with 5% acetone/dichloromethane to give 1-(t-butoxycarbonyl)-4-(1-(fur-2-ylmethyl)-1H-benzimidazole-2-carbonyl)piperidine. Cool 1-(t-butoxycarbonyl)-4-(1-(fur-2-ylmethyl)-1H-benzimidazole-2-carbonyl)piperidine (1.0 mmol), and dichloromethane (5 mL). Slowly add a cold solution of trifluoroacetic acid (1 mmol) in dichloromethane (2 mL). After 15 minutes, partition the reaction mixture between dichloromethane and saturated aqueous sodium bicarbonate solution. Separate the organic layer and extract with brine. Dry the organic layer over Na2SO4, filter, and evaporate invacuo to give the title compound.

Workup

  1. customevaporate the reaction mixture in vacuo
  2. customto give a residue
  3. customPartition the residue between ethyl acetate and water
  4. customSeparate the organic layer
  5. extractionextract with water and saturated aqueous sodium chloride solution
  6. dry with materialDry the organic layer over Na2SO4
  7. filtrationfilter
  8. customevaporate invacuo

Sources & evidence

ORD record
ord-f7dc77cf66c44bed8c0c23fc31eb9690
Source dataset
uspto-grants-1999_12
Patent number
US05998439

Reaction notes

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