Triethylamine → HCID 54569688, compound

HRID 1954828Notes

Reaction equation

HRID 1954828 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=1)[C:11]([OH:13])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:17][C@@H:18]1[CH2:27][CH2:26][C:25]2[C:20](=[CH:21][CH:22]=[CH:23][C:24]=2[N:28]2[CH2:33][CH2:32][N:31]([CH3:34])[CH2:30][CH2:29]2)[CH2:19]1.C(N(CC)CC)C>S(Cl)(Cl)=O.C(Cl)Cl>[CH3:34][N:31]1[CH2:30][CH2:29][N:28]([C:24]2[CH:23]=[CH:22][CH:21]=[C:20]3[C:25]=2[CH2:26][CH2:27][C@@H:18]([NH:17][C:11](=[O:13])[C:10]2[CH:14]=[CH:15][CH:16]=[C:8]([O:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)[CH:9]=2)[CH2:19]3)[CH2:33][CH2:32]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 195393-Phenoxybenzoic acidHCID 53716722HCID 53716722, compound

Product 1

HCID 54569688HCID 54569688, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 24386Thionyl ChlorideSolvent

Procedure

3-Phenoxybenzoic acid (1.0 g, 4.7 mmol) was dissolved in thionyl chloride (15 mL) and heated at reflux for 30 min. The excess of thionyl chloride was evaporated in vacuo, the residue was treated with toluene and again the solvent was removed in vacuo. Crude acid chloride (70 mg, 0.30 mmol) was dissolved in methylene chloride (5 mL) and added dropwise to an ice-cooled solution of (R)-2-amino-5-(4-methylpiperazin-1-yl)-1,2,3,4-tetrahydronaphthalene (70 mg, 0.28 mmol) and triethylamine (55 μL, 0.42 mmol) in methylene chloride (25 mL). After the addition, the reaction was allowed to stir at ambient temperature for 15 min and was then washed with dilute aqueous sodium hydrogen carbonate. The phases were separated and the organic phase was dried (Na2SO4), filtered and evaporated in vacuo to give a crude product which was purified on a silica gel column using chloroform/ethanol saturated with NH3 (100:3) as the eluent. Yield: 45 mg (36%) of the title compound as a solid foam: [α]21D +24° (c 1.0, chloroform); EIMS (70 eV) m/z (relative intensity) 441 (18, M+).

Workup

  1. temperatureheated
  2. temperatureat reflux for 30 min
  3. customThe excess of thionyl chloride was evaporated in vacuo
  4. additionthe residue was treated with toluene
  5. customagain the solvent was removed in vacuo
  6. additionAfter the addition
  7. washwas then washed with dilute aqueous sodium hydrogen carbonate
  8. customThe phases were separated
  9. dry with materialthe organic phase was dried (Na2SO4)
  10. filtrationfiltered
  11. customevaporated in vacuo

Sources & evidence

ORD record
ord-50f70f79df8441e8bdca0918347f0eea
Source dataset
uspto-grants-2000_09
Patent number
US06124283

Reaction notes

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