Triethylamine → HCID 54387466, compound

HRID 1954822Notes

Reaction equation

HRID 1954822 reaction equation
[NH2:1][C@@H:2]1[CH2:11][CH2:10][C:9]2[C:4](=[C:5]([N:12]3[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]3)[CH:6]=[CH:7][CH:8]=2)[CH2:3]1.C(N(CC)CC)C.C([O:29][C:30]1[C:31](=[CH:35][CH:36]=[CH:37][CH:38]=1)[C:32](Cl)=[O:33])(=O)C>C(Cl)Cl>[CH3:18][N:15]1[CH2:16][CH2:17][N:12]([C:5]2[CH:6]=[CH:7][CH:8]=[C:9]3[C:4]=2[CH2:3][C@H:2]([NH:1][C:32](=[O:33])[C:31]2[CH:35]=[CH:36][CH:37]=[CH:38][C:30]=2[OH:29])[CH2:11][CH2:10]3)[CH2:13][CH2:14]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 796682-Acetoxybenzoyl chlorideHCID 53960413(R)-2-amino-8-(4-methylpiperazin-1-yl)-1,2,3,4-tetrahydronaphthalene

Product 1

HCID 54387466HCID 54387466, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To an ice-cooled solution of (R)-2-amino-8-(4-methylpiperazin-1-yl)-1,2,3,4-tetrahydronaphthalene (180 mg, 0.74 mmol) and triethylamine (150 μL, 1.1 mmol) in methylene chloride (20 mL) was added dropwise acetylsalicyloyl chloride (160 mg, 0.78 mmol) in methylene chloride (10 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. The residue was dissolved in 99.5% ethanol (25 mL) and concentrated hydrochloric acid (3 mL) was added. After 17 h, the pH was adjusted to 8 and the solvent was evaporated in vacuo. The residue was partitioned between water and methylene chloride. The organic phase was separated, 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: 170 mg (63%) of the title compound as white crystals: mp 87° C. decomp; [α]21D -18° (c 1.0, chloroform); EIMS (70 eV) m/z (relative intensity) 365 (33, M+).

Workup

  1. additionAfter the addition
  2. washwas then washed with dilute aqueous sodium hydrogen carbonate
  3. customThe phases were separated
  4. dry with materialthe organic phase was dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. dissolutionThe residue was dissolved in 99.5% ethanol (25 mL)
  8. additionconcentrated hydrochloric acid (3 mL) was added
  9. waitAfter 17 h
  10. customthe solvent was evaporated in vacuo
  11. customThe residue was partitioned between water and methylene chloride
  12. customThe organic phase was separated
  13. dry with materialdried (Na2SO4)
  14. filtrationfiltered
  15. customevaporated in vacuo

Sources & evidence

ORD record
ord-0bacb9e1826d484fbd4d18ca4ba24275
Source dataset
uspto-grants-2000_09
Patent number
US06124283

Reaction notes

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