tert-Butyl piperazine-1-carboxylate → HCID 68717618, compound

HRID 1159751Notes

Reaction equation

HRID 1159751 reaction equation
Br[CH2:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH:5]=[CH:6][N:7]2[S:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(=[O:14])=[O:13].C([O-])(O)=O.[Na+].C([N:33]1[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]1)(OC(C)(C)C)=O.C(Cl)(Cl)[Cl:40].CCO>C(O)C>[ClH:40].[C:15]1([S:12]([N:7]2[C:8]3[C:4](=[C:3]([CH2:2][N:33]4[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]4)[CH:11]=[CH:10][CH:9]=3)[CH:5]=[CH:6]2)(=[O:14])=[O:13])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 516892Sodium BicarbonateHCID 19430927HCID 19430927, compoundHCID 21889567Chloroform ethanol

Product 1

HCID 68717618HCID 68717618, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-(Bromomethyl)-1-(phenylsulfonyl)-1H-indole Intermediate 2 (1.025 g), NaHCO3 (1.5 eq) and N—BOC-piperazine (1.5 eq) were refluxed in ethanol for 40 min. The reaction was monitored by TLC (eluent-system CHCl3-EtOH 20:1). The work up of the crude-extraction and further purification by column chromatography (eluent —CHCl3)—yielded the final product as an oil. This material was treated with HCl 5M in i-PrOH to yield the salt of the final product (300 mg, 24%). The synthetic route followed for preparing Example 1 is depicted in the following scheme:

Workup

  1. extractionThe work up of the crude-extraction and further purification by column chromatography (eluent —CHCl3)—yielded the final product as an oil
  2. additionThis material was treated with HCl 5M in i-PrOH

Sources & evidence

ORD record
ord-8cde97eeab9240c5bee7fa9e5c5d2f93
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Reaction notes

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