Triethylamine → 4-Nitrophenyl 4-(pent-4-ynyl)piperazine-1-carboxylate

HRID 417865Notes

Reaction equation

HRID 417865 reaction equation
[CH2:1]([N:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)[CH2:2][CH2:3][C:4]#[CH:5].CCN(CC)CC.Cl[C:20]([O:22][C:23]1[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=1)=[O:21].C(Cl)Cl.CCOC(C)=O>ClCCCl>[CH2:1]([N:6]1[CH2:7][CH2:8][N:9]([C:20]([O:22][C:23]2[CH:24]=[CH:25][C:26]([N+:29]([O-:31])=[O:30])=[CH:27][CH:28]=2)=[O:21])[CH2:10][CH2:11]1)[CH2:2][CH2:3][C:4]#[CH:5]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 821294-Nitrophenyl chloroformateHCID 21226138Dichloromethane ethylacetateHCID 866082211-(Pent-4-yn-1-yl)piperazine

Product 1

HCID 866082224-Nitrophenyl 4-(pent-4-ynyl)piperazine-1-carboxylateYield 64.8%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of 1-(pent-4-ynyl)piperazine (2.2 g) and Et3N (22 mL) in 1,2-dichloroethane (22 mL) was treated with p-nitrophenyl chloroformate (2.9 g) at rt for 10 min. Work-up and silica gel chromatography (DCM:EtOAc 1:3→0:3) gave 4-nitrophenyl 4-(pent-4-ynyl)piperazine-1-carboxylate as a yellow oil (2.96 g).

Sources & evidence

ORD record
ord-ac7df4b6e9f54d9aa0ec390acc7089cb
Source dataset
uspto-grants-2012_01
Patent number
US08093229B2

Reaction notes

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