Pyridine → Diethylether hexane

HRID 2187412Notes

Reaction equation

HRID 2187412 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.N1C=CC=CC=1.[F:25][C:26]([F:37])([F:36])[C:27]([O:29][C:30](=O)[C:31](F)(F)F)=[O:28]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH2:27]([O:29][CH2:30][CH3:31])[CH3:26].[CH3:10][CH2:11][CH2:2][CH2:3][CH2:4][CH3:5].[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:27](=[O:28])[C:26]([F:37])([F:36])[F:25])[CH2:11][CH2:10]3)[CH2:13][CH2:14]1

Participants

7

Reactant 3

HCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 53960413(R)-2-amino-8-(4-methylpiperazin-1-yl)-1,2,3,4-tetrahydronaphthalene

Product 2

HCID 21584099Diethylether hexaneYield 104.4%HCID 54128870(R)-N-[8-(4-Methylpiperazin-1-yl)-1,2,3,4-tetrahydro-2-naphthyl]trifluoroacetamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To an ice-cooled solution of (R)-2-amino-8-(4-methylpiperazin-1-yl)-1,2,3,4-tetrahydronaphthalene (120 mg, 0.49 mmol), pyridine (100 μL, 1.2 mmol) and 4-dimethylaminopyridine (20 mg, 0.16 mmol) in methylene chloride (10 mL) was added dropwise trifluoroacetic anhydride (72 μL, 0.51 mmol). After the addition the reaction was allowed to stir at ambient temperature for 1 h 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 ethyl acetate/methanol/concentrated ammonium hydroxide (96:4:0.5) as the eluent. This gave after crystallization from diethyl ether/hexane 41 mg (24% yield) of the title compound as white crystals: mp 158-159° C.; [α]21D +39° (c 0.25, chloroform); EIMS (70 eV) m/z (relative intensity) 341 (82, M30).

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-5ce8f91333d94c96b07352dc6e6479a5
Source dataset
uspto-grants-2002_06
Patent number
US06410530B1

Reaction notes

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