Water → 3'-({[(4,4-Dimethylcyclohexyl)methyl]amino}methyl)-2-methyl-4-biphenylcarboxamide hydrochloride

HRID 70341Notes

Reaction equation

HRID 70341 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([NH2:17])=[O:16])=[CH:11][C:10]=2[CH3:18])[CH:6]=[CH:7][CH:8]=1)=O.[ClH:19].[CH3:20][C:21]1([CH3:29])[CH2:26][CH2:25][CH:24]([CH2:27][NH2:28])[CH2:23][CH2:22]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O>C(O)(=O)C.CO>[ClH:19].[CH3:20][C:21]1([CH3:29])[CH2:26][CH2:25][CH:24]([CH2:27][NH:28][CH2:1][C:3]2[CH:4]=[C:5]([C:9]3[CH:14]=[CH:13][C:12]([C:15]([NH2:17])=[O:16])=[CH:11][C:10]=3[CH3:18])[CH:6]=[CH:7][CH:8]=2)[CH2:23][CH2:22]1

Participants

7

Reactant 4

HCID 962WaterHCID 5049666Sodium triacetoxyborohydrideHCID 58276414HCID 58276414, compoundHCID 67159793HCID 67159793, compound

Product 1

HCID 671609093'-({[(4,4-Dimethylcyclohexyl)methyl]amino}methyl)-2-methyl-4-biphenylcarboxamide hydrochloride

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 887MethanolSolvent

Procedure

A mixture of 3′-formyl-2-methyl-4-biphenylcarboxamide (0.15 g, 0.63 mmol; Ex. IX-23), 4,4-dimethylcyclohexylmethylamine hydrochloride (0.28 g, 1.6 mmol; Ex III-1) and acetic acid (4 drops) in methanol was stirred at room temperature for 30 min. Sodium triacetoxyborohydride (0.34 g, 1.6 mmol) was added in one portion and the mixture was stirred at room temperature for 72 hr. Water (10 mL) was added and the mixture was stirred at room temperature for 2 hr. The mixture was concentrated in vacuo to remove the methanol and the residue was taken up in a mixture of ethyl acetate and 5% Na2CO3 (aq). The aqueous phase was extracted with ethyl acetate. The combined organic phase was washed with brine, silica gel was added and the mixture was concentrated in vacuo.

Workup

  1. stirringthe mixture was stirred at room temperature for 72 hr
  2. stirringthe mixture was stirred at room temperature for 2 hr
  3. concentrationThe mixture was concentrated in vacuo
  4. customto remove the methanol
  5. additionthe residue was taken up in a mixture of ethyl acetate and 5% Na2CO3 (aq)
  6. extractionThe aqueous phase was extracted with ethyl acetate
  7. washThe combined organic phase was washed with brine, silica gel
  8. additionwas added
  9. concentrationthe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-b301ce448fa246f080cabfb33f4ce09e
Source dataset
uspto-grants-2014_09
Patent number
US08822518B2

Reaction notes

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