Dichloromethane → HCID 89676926, compound

HRID 2278246Notes

Reaction equation

HRID 2278246 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:23]=[CH:22][C:18]([C:19]([OH:21])=O)=[CH:17][C:16]=2[Cl:24])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.CN(C)[CH2:28][CH2:29][CH2:30][N:31]=[C:32]=NCC.ClCCl.N1CCCC1>O>[Cl:24][C:16]1[CH:17]=[C:18]([C:19]([N:31]2[CH2:32][CH2:28][CH2:29][CH2:30]2)=[O:21])[CH:22]=[CH:23][C:15]=1[CH2:14][N:11]1[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7])[CH2:9][CH2:10]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 31268PyrrolidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 89677031HCID 89677031, compound

Product 1

HCID 89676926HCID 89676926, compoundYield 62.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 100 mL round-bottom flask was charged with 4-([4-[(tert-butoxy)carbonyl]piperazin-1-yl]methyl)-3-chlorobenzoic acid (600 mg, 1.69 mmol, 1.00 equiv), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (487 mg, 2.54 mmol, 1.50 equiv), 1-Hydroxybenzotrizole (342 mg, 2.53 mmol, 1.50 equiv), dichloromethane (15 mL). The resulting solution was stirred for 30 min at room temperature and pyrrolidine (240 mg, 3.37 mmol, 2.00 equiv) was added. The resulting solution was stirred for 3 h at room temperature and diluted with H2O (10 mL). The resulting solution was extracted with dichloromethane (3×15 mL) and the organic layers were combined, washed with brine (1×15 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was chromatographed on a silica gel column with ethyl acetate/petroleum ether (80/20) to provide 430 mg (62% yield) of tert-butyl 4-([2-chloro-4-[(pyrrolidin-1-yl)carbonyl]phenyl]methyl)piperazine-1-carboxylate as a white solid. LCMS (ESI, m/z): 408 [M+H]+.

Workup

  1. stirringThe resulting solution was stirred for 3 h at room temperature
  2. extractionThe resulting solution was extracted with dichloromethane (3×15 mL)
  3. washwashed with brine (1×15 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was chromatographed on a silica gel column with ethyl acetate/petroleum ether (80/20)

Sources & evidence

ORD record
ord-bffcf84ae492468f82e59bec64a3fb77
Source dataset
uspto-grants-2015_09
Patent number
US09133148B2

Reaction notes

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