Triethylamine → tert-Butyl 4-(thiophene-2-sulfonyl)piperazine-1-carboxylate

HRID 1365297Notes

Reaction equation

HRID 1365297 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(N(CC)CC)C.[S:21]1[CH:25]=[CH:24][CH:23]=[C:22]1[S:26](Cl)(=[O:28])=[O:27]>C(Cl)Cl>[C:4]([O:3][C:1]([N:8]1[CH2:9][CH2:10][N:11]([S:26]([C:22]2[S:21][CH:25]=[CH:24][CH:23]=2)(=[O:28])=[O:27])[CH2:12][CH2:13]1)=[O:2])([CH3:7])([CH3:6])[CH3:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 855182-Thiophenesulfonyl chlorideHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 17255579tert-Butyl 4-(thiophene-2-sulfonyl)piperazine-1-carboxylateYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To N-Boc-piperazine (500 mg) in DCM (10 ml) was added triethylamine (450 μl) and 2-thiophenesulfonyl chloride (530 mg). The reaction mixture was stirred at room temperature overnight, then partitioned between dichloromethane and water, washed with brine, organics were dried over MgSO4, filtered and volatiles removed in vacuo to give 4-(2-thiophenesulfonyl)-piperazine-1-carboxylic acid tert-butyl ester (759 mg).

Workup

  1. custompartitioned between dichloromethane and water
  2. washwashed with brine
  3. dry with materialorganics were dried over MgSO4
  4. filtrationfiltered
  5. customvolatiles removed in vacuo

Sources & evidence

ORD record
ord-c5b00f3182784632939e78bceb233130
Source dataset
uspto-grants-2011_02
Patent number
US07888352B2

Reaction notes

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