1,4-Dibromobutane → HCID 178453978, compound

HRID 2271569Notes

Reaction equation

HRID 2271569 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:4][CH2:3]1.Br[CH2:17][CH2:18][CH2:19][CH2:20]Br.C(=O)([O-])O.[K+]>CN(C=O)C.[Cl-].[Li+]>[N:1]1([C@H:2]2[CH2:7][CH2:6][C@H:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13])[CH2:4][CH2:3]2)[CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

6

Reactant 3

HCID 80561,4-DibromobutaneHCID 516893Potassium BicarbonateHCID 178419079HCID 178419079, compound

Product 1

HCID 178453978HCID 178453978, compoundYield 16%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 433294Lithium ChlorideSolvent

Procedure

A stirred solution of tert-butyl trans-4-aminocyclohexylcarbamate (2.0 g, 9.33 mmol), 1,4-dibromobutane (1.33 mL, 11.2 mmol), and potassium hydrogen carbonate (4.67 g, 46.7 mmol) in DMF (90 mL) was stirred at room temperature overnight. After this time the reaction was diluted with aqueous lithium chloride and extracted with diethyl ether. The combined organics were dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford the desired product (399 mg, 16%) as an off-white solid: ESI MS m/z 269 [C15H28N2O2+H]+.

Workup

  1. extractionextracted with diethyl ether
  2. dry with materialThe combined organics were dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1c084dcdaa9c4da6ad8b152aa27cfd49
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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