Diethyl Ether → HCID 54487707, compound

HRID 1954778Notes

Reaction equation

HRID 1954778 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][CH3:21])[CH2:14][CH2:13]3)[CH:6]=[CH:7][CH:8]=2)[CH2:3]1.C(N(CC)CC)C.[C:29](Cl)(=[O:31])[CH3:30].C(OCC)C>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:29](=[O:31])[CH3:30])[CH2:11][CH2:10]3)[CH2:13][CH2:14]1)[CH2:19][CH2:20][CH3:21]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 54368073HCID 54368073, compound

Product 1

HCID 54487707HCID 54487707, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To an ice-cooled solution of (R)-2-amino-8-(4-butylpiperazin-1-yl)-1,2,3,4-tetrahydronaphthalene (100 mg, 0.35 mmol) and triethylamine (53 μL, 0.53 mmol) in methylene chloride (25 mL) was added dropwise acetyl chloride (25 ,μL, 0.35 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 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 crystalization from diethyl ether, 100 mg (89% yield) of the title compound as white crystals: mp 118-120° C.; [α]21D +25° (c 0.54, chloroform); EIMS (70 eV) m/z (relative intensity) 329 (41, 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-b3412f07741142c7bea9b9d6760817c7
Source dataset
uspto-grants-2000_09
Patent number
US06124283

Reaction notes

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