Diisopropylethylamine → HCID 11586923, compound

HRID 730752Notes

Reaction equation

HRID 730752 reaction equation
[Br:1][C:2]1[C:3](Cl)=[N:4][CH:5]=[CH:6][CH:7]=1.[CH3:9][C@@H:10]1[CH2:15][NH:14][CH2:13][CH2:12][NH:11]1.C(N(CC)C(C)C)(C)C>CN1C(=O)CCC1>[Br:1][C:2]1[C:3]([N:11]2[CH2:12][CH2:13][NH:14][CH2:15][C@H:10]2[CH3:9])=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 6933243-Bromo-2-chloropyridineHCID 73304342-Methylpiperazine, (R)-

Product 1

HCID 11586923HCID 11586923, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
240 °C

Procedure

A mixture of 3-bromo-2-chloropyridine (2 g, 9 mmol, Aldrich), (R)-(−)-2-methylpiperazine (1.5 g. 15 mmol) and N,N-diisopropylethylamine (1 mL, 5.8 mmol) in NMP (1 mL) was heated in a microwave synthesizer for 60 min at 240° C. The reaction mixture was concentrated and purified by silica gel chromatography, eluting with 10% MeOH in dichloromethane to give 0.5 g (22%) of (2R)-1-(3-bromopyridin-2-yl)-2-methylpiperazine MS (ESI, pos. ion). MS m/z: 256 (M+1), and 0.75 g (33%) of (3R)-1-(3-bromopyridin-2-yl)-3-methylpiperazine. MS m/z: 256 (M+1).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by silica gel chromatography
  3. washeluting with 10% MeOH in dichloromethane

Sources & evidence

ORD record
ord-c8caf0cef2244477b37f2c465e0bb8e7
Source dataset
uspto-grants-2009_09
Patent number
US07582761B2

Reaction notes

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