tert-Butyl piperazine-1-carboxylate → HCID 9865625, compound

HRID 2298038Notes

Reaction equation

HRID 2298038 reaction equation
Cl[C:2]1[C:3]([N+:22]([O-:24])=[O:23])=[C:4]([CH:19]=[CH:20][CH:21]=1)[C:5]([NH:7][CH2:8][C:9]12[CH2:18][CH:13]3[CH2:14][CH:15]([CH2:17][CH:11]([CH2:12]3)[CH2:10]1)[CH2:16]2)=[O:6].[N:25]1(C(OC(C)(C)C)=O)[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1>CS(C)=O.O>[N+:22]([C:3]1[C:2]([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)=[CH:21][CH:20]=[CH:19][C:4]=1[C:5]([NH:7][CH2:8][C:9]12[CH2:18][CH:13]3[CH2:12][CH:11]([CH2:17][CH:15]([CH2:14]3)[CH2:16]1)[CH2:10]2)=[O:6])([O-:24])=[O:23]

Participants

5

Reactant 2

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 11221793HCID 11221793, compound

Product 1

HCID 9865625HCID 9865625, compoundYield 118.8%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 3-chloro-2-nitro-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide (2.80 g, Example 1a) and piperazine-1-carboxylic acid, tert-butyl ester (7.47 g) in dry dimethyl sulfoxide (10 ml) was heated at 120° C. under a nitrogen atmosphere for 24 h. The cooled reaction mixture was diluted with water and extracted thrice with ethyl acetate. The combined extracts were washed with water, dried over sodium sulfate, filtered, and the filtrate concentrated under reduced pressure to give a solid. Purification by chromatography over silica gel, eluting with iso-hexane/ethyl acetate (2:1) gave the subtitle compound as a solid (3.8 g).

Workup

  1. customThe cooled reaction mixture
  2. extractionextracted thrice with ethyl acetate
  3. washThe combined extracts were washed with water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated under reduced pressure
  7. customto give a solid
  8. customPurification by chromatography over silica gel
  9. washeluting with iso-hexane/ethyl acetate (2:1)

Sources & evidence

ORD record
ord-a0ca429bdfc54fc48ed3c60e103b6c6c
Source dataset
uspto-grants-2002_12
Patent number
US06492355B1

Reaction notes

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