Acetyl chloride → HCID 54319692, compound

HRID 1954777Notes

Reaction equation

HRID 1954777 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]([CH2:18][CH2:19][CH3:20])[CH2:14][CH2:13]3)[CH:6]=[CH:7][CH:8]=2)[CH2:3]1.C(N(CC)CC)C.[C:28](Cl)(=[O:30])[CH3:29].C(OCC)(=O)C.CCCCCC>C(Cl)Cl>[CH2:18]([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:28](=[O:30])[CH3:29])[CH2:11][CH2:10]3)[CH2:13][CH2:14]1)[CH2:19][CH3:20]

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 21226206Ethyl acetate hexaneHCID 53934625HCID 53934625, compound

Product 1

HCID 54319692HCID 54319692, compoundYield 93.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To an ice-cooled solution of (R)-2-amino-8-(4-propylpiperazin-1-yl)-1,2,3,4-tetrahydronaphthalene (85 mg, 0.31 mmol) and triethylamine (38 μL, 0.37 mmol) in methylene chloride (15 mL) was added acetyl chloride (23 μL, 0.31 mmol) in methylene chloride (5 mL) dropwise. After the addition the reaction was allowed to stir at ambient temperature for 15 min and was then washed with water. The methylene chloride phase was dried (Na2SO4), filtered and evaporated in vacuo. The residue was purified on a silica gel column using chloroform/ethanol saturated with (NH3) (100:3) as the eluent. This gave 91 mg (93% yield) of the title compound as an oil which was crystallized from ethyl acetate/hexane. Yield: 61 mg (62%) as white crystals: mp 139-140° C.; [α]21D +26° (c 0.50, chloroform); EIMS (70 eV) m/z (relative intensity) 315 (78, M+).

Workup

  1. additionAfter the addition the reaction
  2. washwas then washed with water
  3. dry with materialThe methylene chloride phase was dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe residue was purified on a silica gel column

Sources & evidence

ORD record
ord-41874aadd19344c4ad8e17081a9069ca
Source dataset
uspto-grants-2000_09
Patent number
US06124283

Reaction notes

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