Benzyl piperazine-1-carboxylate → HCID 67054979, compound

HRID 1772784Notes

Reaction equation

HRID 1772784 reaction equation
CC1C=CC(S(O[CH2:12][CH:13]([OH:16])[CH2:14][F:15])(=O)=O)=CC=1.[N:17]1([C:23]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:24])[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1>CO>[F:15][CH2:14][CH:13]([OH:16])[CH2:12][N:20]1[CH2:21][CH2:22][N:17]([C:23]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:24])[CH2:18][CH2:19]1

Participants

4

Reactant 2

HCID 643495Benzyl piperazine-1-carboxylateHCID 155708523-Fluoro-2-hydroxypropyl 4-methylbenzenesulfonate

Product 1

HCID 67054979HCID 67054979, compoundYield 18.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the crude 3-fluoro-2-hydroxypropyl 4-methylbenzenesulfonate (1.98 g, 7.98 mmol) in methanol (40 mL) was added benzyl piperazine-1-carboxylate (1.76 g, 7.98 mmol). The reaction was stirred at RT over the weekend. After being evaporated to dryness, the residue was purified on silica gel, eluting with 0 to 10% MeOH in DCM to yield the desired product (443 mg, 18.7%). LCMS calculated for C15H22FN2O3(M+H)+: m/z=297.2; Found: 297.4.

Workup

  1. customAfter being evaporated to dryness
  2. customthe residue was purified on silica gel
  3. washeluting with 0 to 10% MeOH in DCM

Sources & evidence

ORD record
ord-f029db1cf4364b1f860a592ddb27c323
Source dataset
uspto-grants-2016_02
Patent number
US09249145B2

Reaction notes

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