Acetic Acid → N-benzyl-3,3-bis(4-fluorophenyl)-N-(2-(pyrimidin-2-yl)ethyl)propan-1-amine

HRID 2190321Notes

Reaction equation

HRID 2190321 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[CH2:9][CH:10]=O)=[CH:4][CH:3]=1.[CH2:19]([NH:26][CH2:27][CH2:28][C:29]1[N:34]=[CH:33][CH:32]=[CH:31][N:30]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(O)(=O)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl>[CH2:19]([N:26]([CH2:27][CH2:28][C:29]1[N:30]=[CH:31][CH:32]=[CH:33][N:34]=1)[CH2:10][CH2:9][CH:8]([C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)[C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 183626473,3-Bis(4-fluorophenyl)propanalHCID 68724585N-benzyl-2-(pyrimidin-2-yl)ethanamine

Product 1

HCID 68963034N-benzyl-3,3-bis(4-fluorophenyl)-N-(2-(pyrimidin-2-yl)ethyl)propan-1-amine

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 3,3-bis(4-fluorophenyl)propanal (0.908 g, 3.69 mmol) in DCE (12 mL) at room temperature was added N-benzyl-2-(pyrimidin-2-yl)ethanamine (0.704 g, 3.30 mmol), acetic acid (0.208 g, 3.46 mmol) (0.20 mL). and NaBH(OAc)3 (0.834 g, 3.94 mmol) The reaction mixture was stirred at room temperature for 3 h, quenched with 5 M NaOH (1×), diluted with EtOAc, washed with brine (1×), dried over MgSO4, filtered, and concentrated. Purification by flash column chromatography on silica gel (eluted with 40% to 70% EtOAc in hexanes) gave N-benzyl-3,3-bis(4-fluorophenyl)-N-(2-(pyrimidin-2-yl)ethyl)propan-1-amine.

Workup

  1. customquenched with 5 M NaOH (1×)
  2. additiondiluted with EtOAc
  3. washwashed with brine (1×)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by flash column chromatography on silica gel (eluted with 40% to 70% EtOAc in hexanes)

Sources & evidence

ORD record
ord-94e4c0254e60499aa8c8c6a41a1ea225
Source dataset
uspto-grants-2012_12
Patent number
US08324396B2

Reaction notes

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