Ethyl Acetate → Tert-butyl 4-(3-(4-bromophenoxy)propyl)piperazine-1-carboxylate

HRID 1054687Notes

Reaction equation

HRID 1054687 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][CH2:10][CH2:11]Br)=[CH:4][CH:3]=1.[N:13]1([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1.C([O-])([O-])=O.[Cs+].[Cs+].C(OCC)(=O)C>C(#N)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][CH2:10][CH2:11][N:16]2[CH2:15][CH2:14][N:13]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:18][CH2:17]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 3479241-Bromo-4-(3-bromopropoxy)benzene

Product 1

HCID 86698690Tert-butyl 4-(3-(4-bromophenoxy)propyl)piperazine-1-carboxylateYield 75%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
75 °C

Procedure

To a mixture of 1-bromo-4-(3-bromopropoxy)benzene (300 mg, 1.02 mmol) and tert-butyl piperazine-1-carboxylate (144 mg, 1.02 mmol) in acetonitrile (6.0 mL) was added Cs2CO3 (365 mg, 1.10 mmol). The mixture was stirred at 75° C. for 5 hours. The mixture was poured into ethyl acetate and washed with water. The organic phase was dried over sodium sulfate, filtered, and concentrated to give the title compound (300 mg, 75% yield) as a yellow oil. 1H NMR (400 MHz, CDCl3): δ 7.40 (d, 2 H), 6.75 (d, 2 H), 3.95 (m, 2 H), 3.42 (m, 4 H), 2.54 (t, 2 H), 2.40 (m, 4 H), 2.01-1.89 (m, 2 H), 1.50-1.40 (s, 9 H).

Workup

  1. washwashed with water
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-676a21bc0a2c4f53a23b36e8c26b4956
Source dataset
uspto-grants-2016_07
Patent number
US09394285B2

Reaction notes

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