Sodium borohydride → N-(2-chloro-5-(trifluoromethyl)benzyl)(3,5-bis(trifluoromethyl)phenyl)methanamine

HRID 390757Notes

Reaction equation

HRID 390757 reaction equation
[F:1][C:2]([F:28])([F:27])[C:3]1[CH:4]=[C:5]([CH:20]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:22]=1)[CH:6]=[N:7][CH2:8][C:9]1[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[CH:11][C:10]=1[Cl:19].[BH4-].[Na+]>C(O)C>[Cl:19][C:10]1[CH:11]=[CH:12][C:13]([C:15]([F:16])([F:17])[F:18])=[CH:14][C:9]=1[CH2:8][NH:7][CH2:6][C:5]1[CH:20]=[C:21]([C:23]([F:25])([F:26])[F:24])[CH:22]=[C:3]([C:2]([F:1])([F:27])[F:28])[CH:4]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86614963N-(3,5-bis(trifluoromethyl)benzylidene)(2-chloro-5-(trifluoromethyl)phenyl)methanamine

Product 1

HCID 86614964N-(2-chloro-5-(trifluoromethyl)benzyl)(3,5-bis(trifluoromethyl)phenyl)methanamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of the compound from step A in ethanol was added 4 gm of sodium borohydride and the reaction was allowed to stir overnight at ambient temperature. The reaction was quenched with 50 mL of methanol diluted with 100 mL of water and 100 mL of methyl tert-butyl ether. The layers were separated and the organic layer dried over magnesium sulfate, filtered and concentrated to an oil. 10 gm of desired amine was collected which was used in the next step without further purification. 1H NMR (400 MHz, CDCl3) 7.84 (s, 2H), 7.77 (s, 1H), 7.66 (s, 1H), 7.48 (s, 2H), 7.47 (s, 4H) 13C NMR (400 MHz, CDCl3) 142.6, 1833, 130.4, 128.4, 127.1, 127.0, 125.6, 121.4, 52.4.

Workup

  1. customThe reaction was quenched with 50 mL of methanol
  2. additiondiluted with 100 mL of water and 100 mL of methyl tert-butyl ether
  3. customThe layers were separated
  4. dry with materialthe organic layer dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to an oil
  7. custom10 gm of desired amine was collected which
  8. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-6cc04f1bc24046e0848dd526c1007ed3
Source dataset
uspto-grants-2013_02
Patent number
US08383660B2

Reaction notes

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