1-Benzyl-4-piperidylamine → HCID 59856527, compound

HRID 2378955Notes

Reaction equation

HRID 2378955 reaction equation
[F:1][C:2]1[C:3]([N+:12]([O-:14])=[O:13])=[C:4]([CH2:8][C:9]([OH:11])=O)[CH:5]=[CH:6][CH:7]=1.[CH2:15]([N:22]1[CH2:27][CH2:26][CH:25]([NH2:28])[CH2:24][CH2:23]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O1CCCC1>[CH2:15]([N:22]1[CH2:27][CH2:26][CH:25]([NH:28][C:9](=[O:11])[CH2:8][C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[C:3]=2[N+:12]([O-:14])=[O:13])[CH2:24][CH2:23]1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 4158521-Benzyl-4-piperidylamineHCID 24824213(3-Fluoro-2-nitrophenyl)acetic acid

Product 1

HCID 59856527HCID 59856527, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(3-Fluoro-2-nitrophenyl)acetic acid (1.17 g, 5.88 mmol) was dissolved in tetrahydrofuran (50 ml). N,N′-Carbonyldiimidazole (1.06 g, 6.54 mmol) was added to the mixture in one portion. Reaction stirred at room temperature for 30 minutes. 1-Benzylpiperidin-4-amine (1.15 ml, 6.09 mmol) was added to the mixture in one portion. Reaction stirred at room temperature for 1.25 hours. Reaction was quenched with water. Material was extracted twice with diethyl ether and the aqueous phase was discarded. Material was washed once with water and once with brine and the aqueous phases were discarded. Organics were dried MgSO4, filtered and then concentrated to dryness. Title compound was obtained as amber oil in 99% yield. MS (M+H)+=372.4.

Workup

  1. customReaction
  2. customReaction
  3. stirringstirred at room temperature for 1.25 hours
  4. customReaction
  5. customwas quenched with water
  6. extractionMaterial was extracted twice with diethyl ether
  7. washMaterial was washed once with water and once with brine
  8. filtrationfiltered
  9. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-5b2235ad84d74676919b61d24e7df0dd
Source dataset
uspto-grants-2008_12
Patent number
US07470680B2

Reaction notes

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