3,5-Bis(trifluoromethyl)benzylamine → HCID 23073257, compound

HRID 1157739Notes

Reaction equation

HRID 1157739 reaction equation
[CH:1]1([CH2:6][N:7]([C:10]2[CH:18]=[C:17]3[C:13]([CH2:14][CH2:15][CH2:16]3)=[CH:12][C:11]=2[CH:19]=O)[CH2:8][CH3:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.[F:21][C:22]([F:36])([F:35])[C:23]1[CH:24]=[C:25]([CH:28]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:30]=1)[CH2:26][NH2:27].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[CH:1]1([CH2:6][N:7]([CH2:8][CH3:9])[C:10]2[CH:18]=[C:17]3[C:13](=[CH:12][C:11]=2[CH2:19][NH:27][CH2:26][C:25]2[CH:28]=[C:29]([C:31]([F:32])([F:33])[F:34])[CH:30]=[C:23]([C:22]([F:21])([F:35])[F:36])[CH:24]=2)[CH2:14][CH2:15][CH2:16]3)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 5210993,5-Bis(trifluoromethyl)benzylamineHCID 5049666Sodium triacetoxyborohydrideHCID 230732666-[(Cyclopentylmethyl)ethylamino]-2,3-dihydro-1H-indene-5-carboxaldehyde

Product 1

HCID 23073257HCID 23073257, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution (20 ml) of 6-(N-cyclopentylmethyl-N-ethylamino)indane-5-carbaldehyde (1.09 g) and 3,5-bis(trifluoromethyl)benzylamine (1.26 g) in dichloromethane was added sodium triacetoxyborohydride (1.70 g) with stirring at room temperature. The reaction solution was stirred overnight. The reaction solution was washed successively with saturated aqueous sodium hydrogen carbonate, water and saturated brine, and the organic layer was dried over sodium sulfate. Sodium sulfate was filtered off and the filtrate was concentrated. The obtained residue was purified by column chromatography (n-hexane:ethyl acetate=6:1) to give the title compound (1.65 g, 83%).

Workup

  1. stirringThe reaction solution was stirred overnight
  2. washThe reaction solution was washed successively with saturated aqueous sodium hydrogen carbonate, water and saturated brine
  3. dry with materialthe organic layer was dried over sodium sulfate
  4. filtrationSodium sulfate was filtered off
  5. concentrationthe filtrate was concentrated
  6. customThe obtained residue was purified by column chromatography (n-hexane:ethyl acetate=6:1)

Sources & evidence

ORD record
ord-650b7f08e3b54d85b70f5ef008584858
Source dataset
uspto-grants-2010_10
Patent number
US07807701B2

Reaction notes

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