Water → HCID 51371524, compound

HRID 432878Notes

Reaction equation

HRID 432878 reaction equation
Cl.[CH2:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][C@@H:3]1[NH2:12].C(N(CC)CC)C.[F:20][C:21]1[CH:29]=[CH:28][C:24]([C:25](Cl)=[O:26])=[CH:23][CH:22]=1.O>ClCCl.C(OCC)(=O)C>[F:20][C:21]1[CH:29]=[CH:28][C:24]([C:25]([NH:12][C@H:3]2[CH2:4][CH2:5][C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH2:2]2)=[O:26])=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 678794-Fluorobenzoyl chlorideHCID 49796046HCID 49796046, compound

Product 1

HCID 51371524HCID 51371524, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (S)-1,2,3,4-tetrahydronaphthalen-2-ylamine hydrochloride (0.9 g) in dichloromethane (15 ml) were added in turn triethylamine (1.71 ml) and 4-fluorobenzoyl chloride (0.58 ml) at 0° C. The mixture was allowed to warm to ambient temperature and stirred for 1 hour, which was taken up into a mixture of water and ethyl acetate. The separated organic layer was washed in turn with hydrochloric acid (1N), aqueous sodium hydrogen carbonate and brine, and dried over magnesium sulfate. Evaporation under reduced pressure gave a residue, which was triturated with diisopropyl ether to give (S)-4-fluoro-N-(1,2,3,4-tetrahydro-naphthalen-2-yl)benzamide (1.26 g).

Workup

  1. washThe separated organic layer was washed in turn with hydrochloric acid (1N), aqueous sodium hydrogen carbonate and brine
  2. dry with materialdried over magnesium sulfate
  3. customEvaporation under reduced pressure
  4. customgave a residue, which
  5. customwas triturated with diisopropyl ether

Sources & evidence

ORD record
ord-31b7e1db95d441b38b850430c788ac1b
Source dataset
uspto-grants-2003_12
Patent number
US06664293B2

Reaction notes

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