Triethylamine → HCID 54329100, compound

HRID 1954817Notes

Reaction equation

HRID 1954817 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](=[C:21]([N:28]3[CH2:33][CH2:32][N:31]([CH3:34])[CH2:30][CH2:29]3)[CH:22]=[CH:23][CH:24]=2)[CH2:19]1.C(N(CC)CC)C>S(Cl)(Cl)=O.C(Cl)Cl>[CH3:34][N:31]1[CH2:32][CH2:33][N:28]([C:21]2[CH:22]=[CH:23][CH:24]=[C:25]3[C:20]=2[CH2:19][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)[CH2:27][CH2:26]3)[CH2:29][CH2:30]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 195393-Phenoxybenzoic acidHCID 53960413(R)-2-amino-8-(4-methylpiperazin-1-yl)-1,2,3,4-tetrahydronaphthalene

Product 1

HCID 54329100HCID 54329100, 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 1 h. 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 (99 mg, 0.42 mmol) was dissolved in methylene chloride (5 mL) and added dropwise to an ice-cooled solution of (R)-2-amino-8-(4-methylpiperazin-1-yl)-1,2,3,4-tetrahydronaphthalene (99 mg, 0.41 mmol) and triethylamine (83 μL, 0.42 mmol) in methylene chloride (20 mL). After the addition, the reaction was allowed to stir at ambient temperature for 15 min and was then washed with water. 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: 120 mg (68%) of the title compound as an oil. The oil crystallized from diethyl ether/hexane: mp 136-137° C.; [α]21D -9.0° (c 1.0, chloroform); EIMS (70 eV) m/z (relative intensity) 441 (31, M+).

Workup

  1. temperatureheated
  2. temperatureat reflux for 1 h
  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 water
  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-8c25cdf5620a45f683731732d12324cb
Source dataset
uspto-grants-2000_09
Patent number
US06124283

Reaction notes

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