Trifluoroacetic acid → N-(2,3-dihydro-1H-inden-2-yl)-2,2,2-trifluoroacetamide

HRID 1669528Notes

Reaction equation

HRID 1669528 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3](O)=[O:4].[CH2:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][CH:9]1[NH2:17].CCN(CC)CC>C1COCC1>[F:1][C:2]([F:7])([F:6])[C:3]([NH:17][CH:9]1[CH2:10][C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:8]1)=[O:4]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 763102-Aminoindane

Product 1

HCID 10307996N-(2,3-dihydro-1H-inden-2-yl)-2,2,2-trifluoroacetamideYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under N2 at −75° C., trifluoroacetic acid was added to a stirring solution of 2,3-dihydro-1H-inden-2-amine (HCl salt, 8.0 g, 47.2 mmol), Et3N (14.9 ml, 106.7 mmol) and THF (160 ml). After the solution was allowed to warm up to rt, it was partitioned between H2O and DCM. The organic layer was dried over MgSO4 and evaporated in vacuo. The residue was triturated with hexanes: Et2O (1:1) to obtain the product as a white solid (8.9 g, 82% yield). 1H-NMR (400 MHz, CDCl3) δ 7.28-7.20 (m, 4H), 6.50 (s, 1H), 4.81-4.74 (m, 1H), 3.38 (dd, J=16.4, 7.1 Hz, 2H), 2.89 (dd, J=16.3, 4.2 Hz, 2H).

Workup

  1. customit was partitioned between H2O and DCM
  2. dry with materialThe organic layer was dried over MgSO4
  3. customevaporated in vacuo
  4. customThe residue was triturated with hexanes: Et2O (1:1)

Sources & evidence

ORD record
ord-f07cb177b3a641008c6ccb53cfe3fdb5
Source dataset
uspto-grants-2011_08
Patent number
US07989481B2

Reaction notes

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