HCID 67246961, compound → HCID 57886759, compound

HRID 1430560Notes

Reaction equation

HRID 1430560 reaction equation
[F:1][C:2]1[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][C:3]=1[CH2:4][N:5]1[CH2:9][CH2:8][CH2:7][CH2:6]1>CCOC(C)=O.[Pd]>[F:1][C:2]1[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][C:3]=1[CH2:4][N:5]1[CH2:6][CH2:7][CH2:8][CH2:9]1

Participants

4

Reactant 1

HCID 67246961HCID 67246961, compound

Product 1

HCID 57886759HCID 57886759, compoundYield 72.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-(2-fluoro-5-nitrobenzyl)pyrrolidine (450 mg, 2.007 mmol) in EtOAc (15 mL) was treated with 10% Pd/C (107 mg) and hydrogenated (1 atm) for 3 h. Additional 10% Pd/C (100 mg) was added and the mixture hydrogenated (1 atm) overnight. The solids were removed via filtration through diatomaceous earth, washed with EtOAc and the filtrate washed with water, then brine, dried over Na2SO4 and concentrated to dryness to afford 4-fluoro-3-(pyrrolidin-1-ylmethyl)aniline (282 mg, 72% yield). 1H NMR (400 MHz, DMSO-d6): δ 6.75 (dd, J=10.0, 8.7 Hz, 1H), 6.56 (dd, J=6.4, 2.9 Hz, 1H), 6.39 (ddd, J=8.7, 4.3, 2.9 Hz, 1H), 4.85 (s, 2H), 3.44 (d, J=1.5 Hz, 2H), 2.40 (m, 4H), 1.66 (m, 4H); MS (ESI) m/z: 195.1 [M+H]+.

Workup

  1. customthe mixture hydrogenated (1 atm) overnight
  2. customThe solids were removed via filtration through diatomaceous earth
  3. washwashed with EtOAc
  4. washthe filtrate washed with water
  5. dry with materialbrine, dried over Na2SO4
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-d995705f54184b3bbe2c1a8d837a7da7
Source dataset
uspto-grants-2015_01
Patent number
US08940756B2

Reaction notes

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