Triethylamine → Trifluoroacetamide 2,3-dihydrospiro[indene-1,4'piperidine]

HRID 266889Notes

Reaction equation

HRID 266889 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([NH2:5])=[O:4].[NH:8]1[CH2:13][CH2:12][C:11]2([C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15](=O)[CH2:14]2)[CH2:10][CH2:9]1.C(N(CC)CC)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O>ClCCl.CN(C1C=CN=CC=1)C>[F:1][C:2]([F:7])([F:6])[C:3]([NH2:5])=[O:4].[NH:8]1[CH2:13][CH2:12][C:11]2([C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:15][CH2:14]2)[CH2:10][CH2:9]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 18467060Spiro[1H-indene-1,4'-piperidin]-3(2H)-one trifluoroacetamide

Product 1

HCID 86751117Trifluoroacetamide 2,3-dihydrospiro[indene-1,4'piperidine]

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1.0 g (3.21 mmol) of the intermediate obtained in Step B in 3.0 ml of dichloromethane was added 0.945 ml (6.74 mmol) of triethylamine and 50 mg of DMAP and finally 0.501 ml (3.53 mmol) of trifluroacetic acid anhydride. The reaction mixture was stirred for 3 hours and then diluted with 20 ml of dichloromethane. The solution was washed with water, dried over magnesium sulfate, and concentrated. Purification by flash chromatography (silica gel, hexane/ethyl acetate 2:1) gave 568 mg (1.91 mmol).

Workup

  1. washThe solution was washed with water
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated
  4. customPurification by flash chromatography (silica gel, hexane/ethyl acetate 2:1)
  5. customgave 568 mg (1.91 mmol)

Sources & evidence

ORD record
ord-1b480d20e15a4626a6b5909a4399d08f
Source dataset
uspto-grants-1997_07
Patent number
US05652235

Reaction notes

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