Butylamine → HCID 17223844, compound

HRID 2082305Notes

Reaction equation

HRID 2082305 reaction equation
[F:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([N:8]2[CH2:13][CH2:12][CH:11]([C:14]([OH:16])=O)[CH2:10][CH2:9]2)=[O:7])=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.[CH2:25]([NH2:29])[CH2:26][CH2:27][CH3:28].C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl.O.CN(C)C=O>[CH2:25]([NH:29][C:14]([CH:11]1[CH2:10][CH2:9][N:8]([C:6](=[O:7])[C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:18][CH:17]=2)[CH2:13][CH2:12]1)=[O:16])[CH2:26][CH2:27][CH3:28]

Participants

8

Reactant 4

HCID 8007ButylamineHCID 11430Potassium CarbonateHCID 65578Oxalyl chlorideHCID 7780751-(4-fluorobenzoyl)piperidine-4-carboxylic acid

Product 1

HCID 17223844HCID 17223844, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

1-(4-Fluorobenzoyl)piperidine-4-carboxylic acid (8.79 g, 35.0 mmol) is dissolved in methylene chloride (75 mL) at 0° C., and dimethylformamide (0.20 mL) and oxalyl chloride (4.9 g, 39 mmol) are added. The mixture is stirred at room temperature for 2 hr. In a second flask, butylamine (2.6 g, 35 mmol) and potassium carbonate (9.67 g, 75.4 mmol) are dissolved in water (100 mL) and methylene chloride (200 mL) at 0° C. The first mixture is added to the second dropwise over 45 min, and the mixture is stirred at 0° C. for 2 hr. The organic phase is separated, washed twice with saturated sodium bicarbonate, twice with 1N HCl, dried over magnesium sulfate, and evaporated. Recrystallization from ethyl acetate-hexane affords the title compound.

Workup

  1. customat 0° C
  2. additionThe first mixture is added to the second dropwise over 45 min
  3. stirringthe mixture is stirred at 0° C. for 2 hr
  4. customThe organic phase is separated
  5. washwashed twice with saturated sodium bicarbonate, twice with 1N HCl
  6. dry with materialdried over magnesium sulfate
  7. customevaporated
  8. customRecrystallization from ethyl acetate-hexane

Sources & evidence

ORD record
ord-43a2911f430e4538b1d3e5d9f3aefa92
Source dataset
uspto-grants-1993_02
Patent number
US05189036

Reaction notes

Loading…