Pyridine → HCID 68690521, compound

HRID 1159072Notes

Reaction equation

HRID 1159072 reaction equation
N1C=CC=CC=1.[CH2:7]([N:14]1[CH2:19][C@@H:18]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[NH:17][CH2:16][C@H:15]1[CH3:27])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl[C:29]([O:31][CH3:32])=[O:30]>C(Cl)Cl>[CH2:20]([C@@H:18]1[CH2:19][N:14]([CH2:7][C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[C@H:15]([CH3:27])[CH2:16][N:17]1[C:29]([O:31][CH3:32])=[O:30])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 6586Methyl chloroformateHCID 68686711HCID 68686711, compound

Product 1

HCID 68690521HCID 68690521, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pyridine (0.3 mL, 3.7 mmol) was added to a stirring solution of (2R,5R)-1,5-dibenzyl-2-methylpiperazine (0.28 g, 1.0 mmol) and methyl chloroformate (0.10 g, 0.087 ml, 1.1 mmol) in CH2Cl2 (11 ml). After stirring at ambient temperature for 1 day, the reaction was evaporated in vacuo and the residue purified by flash chromatography (SiO2, 5% MeOH in CH2Cl2) to afford pure product (0.17 g, 49% yield over the two steps). MS (ESI) 339 (M+H).

Workup

  1. customthe reaction was evaporated in vacuo
  2. customthe residue purified by flash chromatography (SiO2, 5% MeOH in CH2Cl2)
  3. customto afford pure product (0.17 g, 49% yield over the two steps)

Sources & evidence

ORD record
ord-9bdf1e9ce862402f9dde255831bc10af
Source dataset
uspto-grants-2010_10
Patent number
US07812024B2

Reaction notes

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