1,4-Dibromobutane → HCID 53810368, compound

HRID 1063354Notes

Reaction equation

HRID 1063354 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Br:15][CH2:16][CH2:17][CH2:18][CH2:19]Br.[H-].[Na+].[NH4+].[Cl-]>CN(C=O)C.CCOCC>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][CH2:19][CH2:18][CH2:17][CH2:16][Br:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 80561,4-DibromobutaneHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Product 1

HCID 53810368HCID 53810368, compoundYield 15%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 10 g (49.7 mmol) 4-Hydroxy-piperidine-1-carboxylic-acid tert-butyl ester and 18 ml (149 mmol) of 1,4-dibromobutane in 100 ml DMF was added under ice-cooling at 0° C., 3.25 g (74.53 mmol) NaH (57% in oil). After 2 h stirring at r.t., 140 ml of sat. NH4Cl-solution was added carefully. The reaction-mixture was diluted with Et2O and washed with water. The organic layer was concentrated in vacuo and the crude product was purified by chromatography on silica gel with Et2O/Hexane 1:2 to yield 2.47 g (15%) of clean 4-(4-Bromo-butoxy)-piperidin-1-carboxylic acid tert-butyl ester, MS: 336 (M+).

Workup

  1. washwashed with water
  2. concentrationThe organic layer was concentrated in vacuo
  3. customthe crude product was purified by chromatography on silica gel with Et2O/Hexane 1:2

Sources & evidence

ORD record
ord-a038c350bc744669b00e0c0bd1114a59
Source dataset
uspto-grants-2005_11
Patent number
US06964974B2

Reaction notes

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