Water → HCID 86585992, compound

HRID 1794068Notes

Reaction equation

HRID 1794068 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14](Cl)=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:17][C:18]1[CH:33]=[CH:32][C:21]([CH2:22][O:23][C:24]2[CH:29]=[CH:28][C:27]([CH2:30][SH:31])=[CH:26][CH:25]=2)=[CH:20][CH:19]=1.O>N1C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([S:31][CH2:30][C:27]2[CH:26]=[CH:25][C:24]([O:23][CH2:22][C:21]3[CH:32]=[CH:33][C:18]([F:17])=[CH:19][CH:20]=3)=[CH:29][CH:28]=2)=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 11334154Tert-butyl 4-(chlorocarbonyl)piperazine-1-carboxylateHCID 222198944-(4-Fluoro-benzyloxy)-phenyl-methanethiol

Product 1

HCID 86585992HCID 86585992, compoundYield 45.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

5.84 g (23.5 mmol) 4-chlorocarbonyl-piperazine-1-carboxylic acid tert-butyl ester were added to a solution of 6.0 g (24.2 mmol) 4-(4-fluoro-benzyloxy)-phenyl-methanethiol in 14.6 ml pyridine. The solution was heated to 100° C. for 3.5 h, then cooled to rt, 10 ml of water added and the volume reduced to a third. The resulting precipitate is collected, washed with water and dried. The crude product is re-crystallized from hexane/AcOEt. Flash chromatography on silica gel provided 4.90 g 4-[4-(4-fluoro-benzyloxy)-benzylsulfanylcarbonyl]-piperazine-1-carboxylic acid tert-butyl ester as colourless powder, mp: 123–124° C. 1H-NMR (CDCl3): 1.46 s, 9H; 3.38–3.60 m, 8H; 4.13 s, 2H; 5.00 s, 2H; 6.89 d, 2H, 7.06 t, 2H, 7.28 d, 2H and 7.40 dd, 2H.

Workup

  1. temperaturecooled to rt
  2. customThe resulting precipitate is collected
  3. washwashed with water
  4. customdried
  5. customThe crude product is re-crystallized from hexane/AcOEt

Sources & evidence

ORD record
ord-72ce5e97c5474011a688e9ecae84b0ae
Source dataset
uspto-grants-2006_04
Patent number
US07022707B2

Reaction notes

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