Sodium Iodide → HCID 59708788, compound

HRID 1097297Notes

Reaction equation

HRID 1097297 reaction equation
[C:1]([O:5][C:6](=[O:13])[NH:7][CH2:8][CH2:9][CH2:10][CH2:11]Br)([CH3:4])([CH3:3])[CH3:2].[CH2:14]([O:21][C:22]([N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1)=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[I-].[Na+].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:14]([O:21][C:22]([N:24]1[CH2:29][CH2:28][N:27]([CH2:11][CH2:10][CH2:9][CH2:8][NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:13])[CH2:26][CH2:25]1)=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 643495Benzyl piperazine-1-carboxylateHCID 10868765tert-butyl N-(4-bromobutyl)carbamate

Product 1

HCID 59708788HCID 59708788, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A solution of (4-bromobutyl)carbamic acid tert-butyl ester (3.75 g, 90%, 13.38 mmol) in acetone (10 mL) was added to a mixture of piperazine-1-carboxylic acid benzyl ester 15 (2.68 g, 12.16 mmol), sodium iodide (1.82 g, 12.16 mmol), and potassium carbonate (5.04 g, 36.47 mmol) in acetone (100 mL). The reaction mixture was stirred at reflux for 24 h. The mixture was concentrated in vacuo, the resulting residue was diluted with dichloromethane and insoluble inorganics were filtered off. The filtrate was concentrated in vacuo and the resulting residue was purified by Biotage silica gel column chromatography using methanol/dichloromethane (gradient 0% to 5%) to give 4-(4-tert-butoxycarbonylaminobutyl)piperazine-1-carboxylic acid benzyl ester (16) as a viscous, brown oil (3.26 g, 68%): 1H NMR (300 MHz, CDCl3) δ 1.40 (s, 9H), 1.51 (m, 4H), 2.49 (m, 6H), 3.10 (m, 2H), 3.51 (m, 4H), 5.10 (s, 2H), 5.25 (br, 1H), 7.32 (m, 5H); ESI MS m/z 392 [C21H33N3O4+H]+.

Workup

  1. temperatureat reflux for 24 h
  2. concentrationThe mixture was concentrated in vacuo
  3. additionthe resulting residue was diluted with dichloromethane and insoluble inorganics
  4. filtrationwere filtered off
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe resulting residue was purified by Biotage silica gel column chromatography

Sources & evidence

ORD record
ord-8d8f69cbb7cb45d0a10d718a12cd008f
Source dataset
uspto-grants-2012_03
Patent number
US08143256B2

Reaction notes

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