4-Phenylbutyric Acid → HCID 54165973, compound

HRID 2187446Notes

Reaction equation

HRID 2187446 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][C:10]([OH:12])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:13][C@@H:14]1[CH2:23][CH2:22][C:21]2[C:16](=[C:17]([N:24]3[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]3)[CH:18]=[CH:19][CH:20]=2)[CH2:15]1.C(N(CC)CC)C>S(Cl)(Cl)=O.C(Cl)Cl>[CH3:30][N:27]1[CH2:28][CH2:29][N:24]([C:17]2[CH:18]=[CH:19][CH:20]=[C:21]3[C:16]=2[CH2:15][C@H:14]([NH:13][C:10](=[O:12])[CH2:9][CH2:8][CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:23][CH2:22]3)[CH2:25][CH2:26]1

Participants

6

Reactant 3

HCID 47754-Phenylbutyric AcidHCID 8471TriethylamineHCID 53960413(R)-2-amino-8-(4-methylpiperazin-1-yl)-1,2,3,4-tetrahydronaphthalene

Product 1

HCID 54165973HCID 54165973, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 24386Thionyl ChlorideSolvent

Procedure

4-Phenylbutyric acid (1.0 g, 6.1 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 (86 mg, 0.47 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 (110 mg, 0.45 mmol) and triethylamine (93 μL, 0.68 mmol) in methylene chloride (15 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 (100:4) as the eluent. Yield: 150 mg (82%) of the title compound as white crystals: mp 137-139° C.; [α]21D +8.4° (c 0.50, chloroform); EIMS (70 eV) m/z (relative intensity) 391 (23, 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-ca5cb7d7bb904e01a263d0a20e69e377
Source dataset
uspto-grants-2002_06
Patent number
US06410530B1

Reaction notes

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