Pyridine → HCID 68688953, compound

HRID 1296290Notes

Reaction equation

HRID 1296290 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 68690258HCID 68690258, compound

Product 1

HCID 68688953HCID 68688953, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pyridine (0.57 ml, 7.0 mmol) was added to a stirring solution of (2S,5R)-1,5-dibenzyl-2-methylpiperazine (0.40 g, 1.2 mmol) and methyl chloroformate (0.20 ml, 2.5 mmol) in CH2Cl2 (14 ml). After stirring at ambient temperature for 2 h, the reaction was evaporated in vacuo and the residue purified by flash chromatography (SiO2, 3% MeOH in CH2Cl2) to afford pure product (0.28 g, 68% 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, 3% MeOH in CH2Cl2)
  3. customto afford pure product (0.28 g, 68% yield over the two steps)

Sources & evidence

ORD record
ord-85185f0c4b4d4dcca039ea8a8b7d8e75
Source dataset
uspto-grants-2007_07
Patent number
US07244843B2

Reaction notes

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