tert-Butyl piperazine-1-carboxylate → 7-(4-t-Butyloxycarbonyl-1-piperazinesulfonyl)-1,2,3,4-tetrahydroisoquinoline

HRID 840140Notes

Reaction equation

HRID 840140 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].FC(F)(F)C([N:18]1[CH2:27][CH2:26][C:25]2[C:20](=[CH:21][C:22]([S:28](Cl)(=[O:30])=[O:29])=[CH:23][CH:24]=2)[CH2:19]1)=O>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([S:28]([C:22]2[CH:21]=[C:20]3[C:25]([CH2:26][CH2:27][NH:18][CH2:19]3)=[CH:24][CH:23]=2)(=[O:29])=[O:30])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 113249022-(Trifluoroacetyl)-1,2,3,4-tetrahydroisoquinoline-7-sulfonyl chloride

Product 1

HCID 187651757-(4-t-Butyloxycarbonyl-1-piperazinesulfonyl)-1,2,3,4-tetrahydroisoquinolineYield 35%

Procedure

The subtitle compound was prepared by the method of Example 16(a) from 1-t-butyloxycarbonylpiperazine and 2-trifluoroacetyl-1,2,3,4-tetrahydroisoquinoline-7-sulfonyl chloride. The product was purified on silica gel, eluting with CH2Cl2/MeOH (93/7, v/v) to afford the subtitle compound (35%) as a colourless solid. Rf 0.56 (CH2Cl2/MeOH 9/1, v/v). MS m/z 382 (MH+).

Workup

  1. customThe product was purified on silica gel
  2. washeluting with CH2Cl2/MeOH (93/7

Sources & evidence

ORD record
ord-88ab39841abc4dadb85c33a6baa76ef3
Source dataset
uspto-grants-2002_04
Patent number
US06365599B1

Reaction notes

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