Acetic Acid → HCID 178468170, compound

HRID 1968950Notes

Reaction equation

HRID 1968950 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[OH:9].[CH2:10]([O:12][C@H:13]1[CH2:18][CH2:17][C@H:16]([N:19]2[CH2:24][CH2:23][C:22](=O)[CH2:21][CH2:20]2)[CH2:15][CH2:14]1)[CH3:11].C([BH3-])#N.[Na+].C(O)(=O)C>ClCCl>[CH2:10]([O:12][C@H:13]1[CH2:14][CH2:15][C@H:16]([N:19]2[CH2:24][CH2:23][CH:22]([NH:1][C:2]3[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=3[OH:9])[CH2:21][CH2:20]2)[CH2:17][CH2:18]1)[CH3:11]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 72642-Amino-4-methylphenolHCID 5003444Sodium cyanoborohydrideHCID 178468171HCID 178468171, compound

Product 1

HCID 178468170HCID 178468170, compoundYield 141.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Amino-4-methylphenol (56.1 mg, 0.456 mmol) was dissolved in dichloromethane (3 mL) and 1-[trans-4-(ethyloxy)cyclohexyl]-4-piperidinone (D66, 103 mg, 0.456 mmol), polymer supported sodium cyanoborohydride (212 mg, 0.912 mmol, 4.3 mmol/g) and acetic acid (0.13 mL, 2.28 mmol) were all added at rt. The mixture was reacted at 100° C. in the microwave for 10 min. The mixture was then cooled to rt, filtered and concentrated by rotary evaporation to give 2-({1-[trans-4-(ethyloxy)cyclohexyl]-4-piperidinyl}amino)-4-methylphenol (D29, 215 mg, 92% yield) as a white solid.

Workup

  1. additionall added at rt
  2. customThe mixture was reacted at 100° C. in the microwave for 10 min
  3. filtrationfiltered
  4. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-f12a91ae52954796aa2b3d42e89502f7
Source dataset
uspto-grants-2013_04
Patent number
US08426443B2

Reaction notes

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