1-(2-Chloroethyl)pyrrolidine → 3-Bromo-5-fluoro-N-(2-(pyrrolidin-1-yl)ethyl)aniline

HRID 1049916Notes

Reaction equation

HRID 1049916 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([F:9])[CH:8]=1)[NH2:5].Cl[CH2:11][CH2:12][N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1>CN1C(=O)CCC1.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([F:9])[CH:8]=1)[NH:5][CH2:11][CH2:12][N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

5

Reactant 2

HCID 816691-(2-Chloroethyl)pyrrolidineHCID 150201553-Bromo-5-fluoroaniline

Product 1

HCID 867039193-Bromo-5-fluoro-N-(2-(pyrrolidin-1-yl)ethyl)anilineYield 50.5%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 3-bromo-5-fluoroaniline (CAS 134168-97-1) (380 mg, 2.0 mmol) and 1-(2-chloroethyl)pyrrolidine (CAS 505041-9) (380 mg, 2.2 mmol) in NMP (20 mL) was heated to 120° C. overnight. The solution was diluted with EtOAc (100 mL) and washed with saturated Na2CO3 aqueous solution (3×40 mL). The combined organic layer were dried over Na2SO4, concentrated and purified by prep-TLC (DCM:MeOH=10:1) to give the titled product (290 mg, 50%). LCMS (0-60 AB), RT=1.076 min, M+H, 289.0

Workup

  1. washwashed with saturated Na2CO3 aqueous solution (3×40 mL)
  2. dry with materialThe combined organic layer were dried over Na2SO4
  3. concentrationconcentrated
  4. custompurified by prep-TLC (DCM:MeOH=10:1)

Sources & evidence

ORD record
ord-10655e0ff1c3493fb7cb518d8ef8caac
Source dataset
uspto-grants-2016_07
Patent number
US09382241B2

Reaction notes

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