6-Aminohexanoic Acid → HCID 2054805, compound

HRID 2276710Notes

Reaction equation

HRID 2276710 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8].C([O-])([O-])=O.[Na+].[Na+].[Br:16][C:17]1[CH:25]=[CH:24][C:20]([C:21](Cl)=[O:22])=[CH:19][CH:18]=1>O>[Br:16][C:17]1[CH:25]=[CH:24][C:20]([C:21]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8])=[O:22])=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 5646-Aminohexanoic AcidHCID 10340Sodium CarbonateHCID 685154-Bromobenzoyl chloride

Product 1

HCID 2054805HCID 2054805, compoundYield 61.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 6-aminohexanoic acid (5.0 g, 38.7 mmol), Na2CO3 (4.1 g, 38.7 mmoL) in water (100 mL) was added drop-wise 4-bromobenzoyl chloride (8.5 g, 38.7 mmoL, dissolved in 80 mL THF) at 0° C. and stirred for 4 hours. The mixture was concentrated under reduced pressure. The pH value of the solution was adjusted to 1 by concentrated HCl. The resulting mixture was extracted by EtOAc (200 mL×3). The organic layers were combined and dried over Na2SO4, then concentrated to give the desired compound (7.5 g, yield 61.7%).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. extractionThe resulting mixture was extracted by EtOAc (200 mL×3)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-be15215b87134bbd892b62cc506e0947
Source dataset
uspto-grants-2015_09
Patent number
US09133105B2

Reaction notes

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