p-Fluoronitrobenzene → HCID 21105671, compound

HRID 1963033Notes

Reaction equation

HRID 1963033 reaction equation
[CH3:1][NH:2][CH:3]1[CH2:7][CH2:6][NH:5][CH2:4]1.F[C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=1>>[CH3:1][NH:2][CH:3]1[CH2:7][CH2:6][N:5]([C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=2)[CH2:4]1

Participants

3

Reactant 2

HCID 9590p-FluoronitrobenzeneHCID 117882683-(Methylamino)pyrrolidine

Product 1

HCID 21105671HCID 21105671, compound

Conditions

Temperature
110 °C

Procedure

N-methylpyrrolidin-3-amine (0.788 g, 7.87 mmol) was added to 1-fluoro-4-nitrobenzene (1.11 g, 7.87 mmol) slowly (CAUTION: extreme exotherm!!!). The resulting mixture was heated at 110° C. for 10 min. After cooling down to room temperature, another portion of amine (0.156 g) was added to the reaction mixture. The resulting mixture was heated at 110° C. for 1 h. After cooling down to room temperature, the obtained black solid product (Example 43A) was used for next step without further purification. LCMS (ES): m/z 252.3 [M+H]+.

Workup

  1. temperatureAfter cooling down to room temperature
  2. temperatureThe resulting mixture was heated at 110° C. for 1 h
  3. temperatureAfter cooling down to room temperature
  4. customthe obtained black solid product (Example 43A) was used for next step without further purification

Sources & evidence

ORD record
ord-afda142d63c2496d8da88ada5192b63e
Source dataset
uspto-grants-2013_04
Patent number
US08415386B2

Reaction notes

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