1-Pyrrolidineethanamine → HCID 69299992, compound

HRID 131280Notes

Reaction equation

HRID 131280 reaction equation
F[C:2]1[CH:14]=[CH:13][C:5]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])=[CH:4][CH:3]=1.[NH2:15][CH2:16][CH2:17][N:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1>O>[N:18]1([CH2:17][CH2:16][NH:15][C:2]2[CH:14]=[CH:13][C:5]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])=[CH:4][CH:3]=2)[CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

4

Reactant 2

HCID 13441-PyrrolidineethanamineHCID 2736444Tert-butyl 4-fluorobenzoate

Product 1

HCID 69299992HCID 69299992, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of tert-butyl 4-fluorobenzoate (2.14 g) and 1-(2-aminoethyl)pyrrolidine (1 mL) is stirred at 120° C. for one day. After cooling, to the reaction mixture is added water and the mixture is extracted with ethyl acetate (×2). The extract is concentrated by centrifugal concentrator and the residue is purified by flash column chromatography on NH-silica gel (Solvent; n-hexane:ethyl acetate=8:1→4:1) to give tert-butyl 4-[[2-(1-pyrrolidinyl)ethyl]amino]benzoate (1.62 g, yield; 51%) as an oil. MS (APCI) m/z: 291 [M+H]+

Workup

  1. temperatureAfter cooling, to the reaction mixture
  2. extractionthe mixture is extracted with ethyl acetate (×2)
  3. concentrationThe extract is concentrated by centrifugal concentrator
  4. customthe residue is purified by flash column chromatography on NH-silica gel (Solvent; n-hexane:ethyl acetate=8:1→4:1)

Sources & evidence

ORD record
ord-e02528d578e044078b957fe836e2bf39
Source dataset
uspto-grants-2008_06
Patent number
US07384952B2

Reaction notes

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