6-Aminohexanoic Acid → HCID 14196779, compound

HRID 1776128Notes

Reaction equation

HRID 1776128 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[NH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18]>CN(C1C=CN=CC=1)C.C1COCC1>[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 5646-Aminohexanoic AcidHCID 134054-Methylbenzoyl Chloride

Product 1

HCID 14196779HCID 14196779, compoundYield 43.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

4-Methylbenzoyl chloride (1.46 g, 9.5 mmol) was added dropwise to a mixture of 6-aminohexanoic acid (1.31 g, 10 mmol) and DMAP (1.22 g, 10 mmol) in THF (100 mL) at 0° C. The mixture was warmed to room temperature and stirred overnight. THF was evaporated, and dichloromethane (100 mL) was added. The mixture was washed with water and brine, dried over Na2SO4, and evaporated. The residue was purified by chromatography on silica gel to give the title compound (1.03 g, 41.5%).

Workup

  1. customTHF was evaporated
  2. additiondichloromethane (100 mL) was added
  3. washThe mixture was washed with water and brine
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-d2718757f1134eb79c7540480c8aac40
Source dataset
uspto-grants-2016_02
Patent number
US09265734B2

Reaction notes

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