HCID 59401866, compound → 4-[3-(2-Methylpyrrolidin-1-yl)pyrrolidin-1-yl]aniline

HRID 391177Notes

Reaction equation

HRID 391177 reaction equation
[CH3:1][CH:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH:7]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[C:14](C)[CH:13]=2)[CH2:8]1>CO.C(Cl)Cl.[Pd]>[CH3:1][CH:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH:7]1[CH2:11][CH2:10][N:9]([C:12]2[CH:13]=[CH:14][C:15]([NH2:18])=[CH:16][CH:17]=2)[CH2:8]1

Participants

5

Reactant 1

HCID 59401866HCID 59401866, compound2×

Product 1

HCID 666252224-[3-(2-Methylpyrrolidin-1-yl)pyrrolidin-1-yl]aniline

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-methyl-1′-(3-methyl-4-nitro-phenyl)[1,3′]bipyrrolidinyl (Intermediate (iii) obtained above, 2.23 g, 7.7 mmol) in MeOH was de-aerated and nitrogen was introduced. To this solution was added Pd—C (10%). This mixture was stirred under H2 atmosphere at r.t. for 8 h. TLC (10% MeOH in DCM) and LC/MS showed the reaction was complete. The mixture was passed through a Celite pad, rinsed with methanol. The filtrate was concentrated to dryness, and further dried under high vacuum to yield a reddish brown liquid after drying under high vacuum to obtain the title compound as a gummy black liquid, 1.73 g (86%). This material was used in the next step without further purification and storage. MS: 260 (M+H+).

Workup

  1. additionnitrogen was introduced
  2. washrinsed with methanol
  3. concentrationThe filtrate was concentrated to dryness
  4. customfurther dried under high vacuum
  5. customto yield a reddish brown liquid
  6. customafter drying under high vacuum

Sources & evidence

ORD record
ord-0af47d4bf37446cfacc8098a6fee5c80
Source dataset
uspto-grants-2013_02
Patent number
US08383814B2

Reaction notes

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