Formaldehyde → N-{2,6-Dimethyl-4-[methyl-(4-trifluoromethyl-benzyl)-amino]-phenyl}-acetamide

HRID 1820148Notes

Reaction equation

HRID 1820148 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)[CH:5]=[C:4]([CH3:20])[C:3]=1[NH:21][C:22](=[O:24])[CH3:23].C=O.[C:27]([BH3-])#N.[Na+]>CO.C(O)(=O)C>[CH3:1][C:2]1[CH:7]=[C:6]([N:8]([CH3:27])[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:18])([F:19])[F:17])=[CH:12][CH:11]=2)[CH:5]=[C:4]([CH3:20])[C:3]=1[NH:21][C:22](=[O:24])[CH3:23]

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 11652937N-[2,6-Dimethyl-4-(4-trifluoromethyl-benzylamino)-phenyl]-acetamide

Product 1

HCID 11638852N-{2,6-Dimethyl-4-[methyl-(4-trifluoromethyl-benzyl)-amino]-phenyl}-acetamideYield 60.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Conditions

Temperature
5 °C

Procedure

To a stirred solution of N-[2,6-dimethyl-4-(4-trifluoromethyl-benzylamino)-phenyl]-acetamide (4a, 1.0 g) and formaldehyde (1 mL) in methanol (20 mL) and acetic acid (1 mL) was slowly added sodium cyanoborohydride (0.30 g). After 15 minutes, the reaction mixture was cooled to 5° C. for 16 hours to precipitate the product, which was collected by filtration and washed with water (100 mL) to furnish 0.63 g (60% yield) of the title compound as a pale yellow solid. LC-MS-TOF (m/z) 351 (MH+); tR=2.58, (UV, ELSD) 99%, 99%. 1H NMR (500 MHz, DMSO-d6): 1.97 (s, 3H), 2.02 (s, 6H), 2.97 (s, 3H), 4.63 (s, 2H), 7.41 (d, 2H), 7.68 (d, 2H), 8.88 (s, 1H).

Workup

  1. customto precipitate the product, which
  2. filtrationwas collected by filtration
  3. washwashed with water (100 mL)

Sources & evidence

ORD record
ord-38c97ae7afdd42388d166077af16dfa7
Source dataset
uspto-grants-2009_10
Patent number
US07601870B2

Reaction notes

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