Acetyl chloride → Diethylether hexane

HRID 1954780Notes

Reaction equation

HRID 1954780 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][CH2:20][CH2:21][CH2:22][CH3:23])[CH2:14][CH2:13]3)[CH:6]=[CH:7][CH:8]=2)[CH2:3]1.C(N(CC)CC)C.[C:31](Cl)(=[O:33])[CH3:32]>C(Cl)Cl>[CH2:31]([O:33][CH2:22][CH3:23])[CH3:32].[CH3:10][CH2:11][CH2:2][CH2:3][CH2:4][CH3:5].[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:31](=[O:33])[CH3:32])[CH2:11][CH2:10]3)[CH2:13][CH2:14]1)[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 53645591HCID 53645591, compound

Product 2

HCID 21584099Diethylether hexaneYield 370.3%HCID 54515462HCID 54515462, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To an ice-cooled solution of (R)-2-amino-8-(4-hexylpiperazin-1-yl)-1,2,3,4-tetrahydronaphthalene (97 mg, 0.31 mmol) and triethylamine (51 μL, 0.37 mmol) in methylene chloride (15 mL) was added dropwise acetyl chloride (23 μL, 0.32 mmol) in methylene chloride (5 mL). 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 after crystallization from diethyl ether/hexane 92 mg (83% yield) of the title compound as white crystals: mp 117-118° C.; [α]21D +19° (c 1.0, chloroform); EIMS (70 eV) m/z (relative intensity) 357 (43, 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
  7. customThis gave

Sources & evidence

ORD record
ord-43e1492714c84d1fa6bf5e71ebe8cb90
Source dataset
uspto-grants-2000_09
Patent number
US06124283

Reaction notes

Loading…