2-Pyridineethanamine → 3,3-bis(4-fluorophenyl)-N-(2-(pyridin-2-yl)ethyl)propan-1-amine

HRID 2190303Notes

Reaction equation

HRID 2190303 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.[N:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH2:25][CH2:26][NH2:27].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl.CCOC(C)=O>[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][CH2:10][NH:27][CH2:26][CH2:25][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][N:19]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 759192-PyridineethanamineHCID 5049666Sodium triacetoxyborohydrideHCID 183626473,3-Bis(4-fluorophenyl)propanal

Product 1

HCID 575864323,3-bis(4-fluorophenyl)-N-(2-(pyridin-2-yl)ethyl)propan-1-amine

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3,3-bis(4-fluorophenyl)propanal (0.967 g, 3.93 mmol) in DCE (15 mL) at room temperature was added 2-(pyridin-2-yl)ethanamine (1.73 g, 14.2 mmol) and NaBH(OAc)3 (1.08 g, 5.10 mmol). The reaction mixture was stirred at room temperature for 17 h, diluted with EtOAc, washed with 5 M NaOH (1×), brine (1×), dried over MgSO4, filtered, and concentrated. Purification by flash column chromatography on silica gel (eluted with 2% to 8% MeOH (2M NH3) in DCM) followed by purification by flash column chromatography on silica gel (eluted with 50% to 100% EtOAc (10% 2M NH3 in MeOH) in hexanes) gave 3,3-bis(4-fluorophenyl)-N-(2-(pyridin-2-yl)ethyl)propan-1-amine.

Workup

  1. washwashed with 5 M NaOH (1×), brine (1×)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by flash column chromatography on silica gel (eluted with 2% to 8% MeOH (2M NH3) in DCM)
  6. customfollowed by purification by flash column chromatography on silica gel (eluted with 50% to 100% EtOAc (10% 2M NH3 in MeOH) in hexanes)

Sources & evidence

ORD record
ord-f5d75d298ae24a7384bbd46d6df459dd
Source dataset
uspto-grants-2012_12
Patent number
US08324396B2

Reaction notes

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