tert-Butyl piperazine-1-carboxylate → HCID 69519830, compound

HRID 1180009Notes

Reaction equation

HRID 1180009 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][N:13]=2)=[CH:7][CH:6]=1)=[O:3].[C:22]([O:26][C:27]([N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1)=[O:28])([CH3:25])([CH3:24])[CH3:23].[K+].[Br-]>CCOC(C)=O.CCCCCCC>[F:19][C:18]([F:21])([F:20])[C:15]1[CH:16]=[CH:17][C:12]([O:11][C:8]2[CH:9]=[CH:10][C:5]([O:4][C:2]([N:32]3[CH2:31][CH2:30][N:29]([C:27]([O:26][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:28])[CH2:34][CH2:33]3)=[O:3])=[CH:6][CH:7]=2)=[N:13][CH:14]=1

Participants

5

Reactant 3

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 253877Potassium BromideHCID 220477624-(5-Trifluoromethylpyridin-2-yloxy)-phenyl chloroformate

Product 1

HCID 69519830HCID 69519830, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 21899848Ethylacetate heptaneSolvent

Procedure

The title compound was prepared from 4-(5-trifluoromethyl-pyridin-2-yloxy)-phenyl chloroformate and 1-tert-butoxycarbonyl-piperazin, yield 59% (recrystallized from EtOAc—heptane 1:1). White crystals, m.p. 165-166° C.; 1H NMR (CDCl3) □ 8.45-8.42 (m, 1H), 7.92-7.87 (m, dd-like, 1H), 7.21-7.12 (AB-system, 4H), 7.03-6.98 (m, d-like, 1H), 3.72-3.45 (br m, 8H), 1.49 (s, 9H); 13C-NMR (CDCl3) □ (ref. CDCl3 77.00 ppm):165.71, 154.56, 153.51, 150.21, 148.34, 145.43 (q, J=4.4 Hz), 136.701 (q, J=3 Hz), 123.65 (q, J=271.5 Hz), 122.86, 122.24, 121.62 (q, J=33 Hz), 11.20, 80.32, 44.38, 43.78, 44.6-42.3 (br), 28.36 ppm; IR (KBr) □ 1722 (C═O), 1691 (C═O) cm−1.

Sources & evidence

ORD record
ord-fea052bf905e450daf2971ed7f734c42
Source dataset
uspto-grants-2007_10
Patent number
US07279470B2

Reaction notes

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