Sodium Hydroxide → (r)-n-[5-Bromo-8-(4-methylpiperazin-1-yl)-1,2,3,4-tetrahydro-2-naphthyl]-4-trifluoromethylbenzamide

HRID 427347Notes

Reaction equation

HRID 427347 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:9]=[CH:10][CH:11]=[C:12]3[C:17]=2[CH2:16][C@H:15]([NH:18][C:19](=[O:30])[C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=2)[CH2:14][CH2:13]3)[CH2:4][CH2:3]1.C([O-])(=O)C.[Na+].[Br:36]Br.[OH-].[Na+]>C(O)(=O)C>[Br:36][C:11]1[CH:10]=[CH:9][C:8]([N:5]2[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]2)=[C:17]2[C:12]=1[CH2:13][CH2:14][C@@H:15]([NH:18][C:19](=[O:30])[C:20]1[CH:21]=[CH:22][C:23]([C:26]([F:29])([F:27])[F:28])=[CH:24][CH:25]=1)[CH2:16]2

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 24408BromineHCID 517045Sodium AcetateHCID 53714488(R)-N-[8-(4-Methylpiperazin-1-yl)-1,2,3,4-tetrahydro-2-naphthyl]-4-trifluoromethylbenzamide

Product 1

HCID 53698276(r)-n-[5-Bromo-8-(4-methylpiperazin-1-yl)-1,2,3,4-tetrahydro-2-naphthyl]-4-trifluoromethylbenzamideYield 85%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

(R)-N-[8-(4-methylpiperazin-1-yl)-1,2,3,4-tetrahydro-2-naphthyl]-4-trifluoromethylbenzamide (80 mg, 0.19 mmol) and sodium acetate (200 mg) were dissolved in acetic acid (3 mL) and the mixture was stirred at room temperature. Bromine (34 mg, 0.21 mmol) was added dropwise to the reaction mixture and the mixture was stirred for 2 h at ambient temperature. A 2 M sodium hydroxide solution (100 mL) was added and the mixture was extracted with diethyl ether (2×50 mL). The combined organic phases were dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. Purification on a silica gel column using methylene chloride/ethanol saturated with NH3 (94:6) as the eluent gave 80 mg (85% yield) of the title compound as a white solid: mp 229-230° C.; [αC]21D−5.4° (c=1, chloroform); EIMS (70 eV) m/z (relative intensity) 495 and 497 (3, M+).

Workup

  1. stirringthe mixture was stirred for 2 h at ambient temperature
  2. extractionthe mixture was extracted with diethyl ether (2×50 mL)
  3. dry with materialThe combined organic phases were dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification on a silica gel column

Sources & evidence

ORD record
ord-a174d78abf5c475ebfa489a412c39291
Source dataset
uspto-grants-2001_11
Patent number
US06313118B1

Reaction notes

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