1,2-Dichloroethane → HCID 57597100, compound

HRID 1747243Notes

Reaction equation

HRID 1747243 reaction equation
[N:1]1([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[N+:14]([C:17]1[CH:18]=[C:19]([CH2:23][C:24](O)=[O:25])[CH:20]=[CH:21][CH:22]=1)([O-:16])=[O:15].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C>CCOC(C)=O>[N+:14]([C:17]1[CH:18]=[C:19]([CH2:23][C:24]([N:4]2[CH2:5][CH2:6][N:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:2][CH2:3]2)=[O:25])[CH:20]=[CH:21][CH:22]=1)([O-:16])=[O:15]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 158763-Nitrophenylacetic acid2×HCID 757711-HydroxybenzotriazoleHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 57597100HCID 57597100, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

An oven-dried, round-bottom flask was charged with tert-butyl piperazine-1-carboxylate (1.1 eq), 3-nitrophenylacetic acid (7A, 1.0 eq), EDC (1.2 eq), and HOBT (1.2 eq). The flask was flushed with nitrogen, and N,N-dimethylformamide (about 0.5 M 7A in DMF) and triethylamine (2.0 eq) were added by syringe. The resulting reaction mixture was stirred overnight at room temperature. The reaction mixture was then diluted with EtOAc, and washed 4 times with H2O, twice with 1 N aq. KHSO4, once with saturated NaHCO3, and once with brine. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo. Tert-butyl 4-(2-(3-nitrophenyl)acetyl)piperazine-1-carboxylate (7B) was isolated as a solid (80%) and used without further purification.

Workup

  1. additionwere added by syringe
  2. customThe resulting reaction mixture
  3. washwashed 4 times with H2O
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-58726dd6e1214e6889fe2229ed3e1d86
Source dataset
uspto-grants-2015_10
Patent number
US09150564B2

Reaction notes

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