Acetyl chloride → HCID 54490053, compound

HRID 2187406Notes

Reaction equation

HRID 2187406 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:26](Cl)(=[O:28])[CH3:27].C(Cl)(Cl)Cl.CO>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:26](=[O:28])[CH3:27])[CH2:11][CH2:10]3)[CH2:13][CH2:14]1

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 21584188Chloroform methanolHCID 53960413(R)-2-amino-8-(4-methylpiperazin-1-yl)-1,2,3,4-tetrahydronaphthalene

Product 1

HCID 54490053HCID 54490053, compoundYield 93.4%

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 (100 mg, 0.41 mmol) and triethylamine (110 μL, 0.82 mmol) in methylene chloride (25 mL) was added acetyl chloride (31 μL, 0.43 mmol) in methylene chloride (10 mL). After the addition the reaction was allowed to reach room temperature and then washed with water. The phases were separated, the combined organic phases were dried (Na2SO4), filtered and evaporated in vacuo to give a crude product which was purified on a silica get column using chloroform/methanol/concentrated ammonium hydroxide (95:4:0.5) as the eluent. Yield: 110 mg (90%) of the title compound as an oil. Crystallization from ethyl acetate/hexane gave 52 mg (44% yield) of white crystals: mp 152-154° C.; [α]21D +66° (c 0.13, chloroform); EIMS (70 eV) m/z (relative intensity) 287 (9, M+).

Workup

  1. additionAfter the addition the reaction
  2. customto reach room temperature
  3. washwashed with water
  4. customThe phases were separated
  5. dry with materialthe combined organic phases were dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customto give a crude product which
  9. customwas purified on a silica
  10. customget column

Sources & evidence

ORD record
ord-6591a6046b76493abb1f345a8ffefb7a
Source dataset
uspto-grants-2002_06
Patent number
US06410530B1

Reaction notes

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