Cyclohexylamine → HCID 10423850, compound

HRID 1781177Notes

Reaction equation

HRID 1781177 reaction equation
[O:1]([C:8]1[CH:15]=[CH:14][C:11]([CH:12]=O)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:16]1([NH2:22])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.C([BH3-])#N.[Na+]>CO>[CH:16]1([NH:22][CH2:12][C:11]2[CH:14]=[CH:15][C:8]([O:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:9][CH:10]=2)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 7965CyclohexylamineHCID 661394-PhenoxybenzaldehydeHCID 5003444Sodium cyanoborohydride

Product 1

HCID 10423850HCID 10423850, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-Phenoxybenzaldehyde (5.0 g, 25.0 mmol) and cyclohexylamine (2.5 g, 25 mmol) were dissolved in methanol (85 mL) under nitrogen at room temperature. Sodium cyanoborohydride (1.57 g, 25.0 mmol) was added, and stirring was continued for 48 hours. The solvent was evaporated and the residue was suspended in ether, washed with brine, and dried over Na2SO4. The ether was evaporated, and the crude product was chromatographed on silica gel eluting with 3% methanol in methylene chloride to provide 6.4 g (91%) of the title compound as a colorless oil. 1H NMR (CDCl3, 300 MHz) δ 1.05-1.35 (m, 5H), 1.55-1.65 (m, 1H), 1.70-1.80 (m, 3H), 1.85-2.00 (m, 2H), 2.45-2.55 (m, 1 H) 3.80 (s, 2H), 6.95-7.04 (m, 4H), 7.05 (tt, J=7.5, 1.5 Hz, 1H), 7.25-7.35 (m, 4H). MS (DCl/NH3) m/e 282 (M+H)+.

Workup

  1. customThe solvent was evaporated
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. customThe ether was evaporated
  5. customthe crude product was chromatographed on silica gel eluting with 3% methanol in methylene chloride

Sources & evidence

ORD record
ord-a49a6c730e16434c9a15d096a5231002
Source dataset
uspto-grants-1997_05
Patent number
US05631401

Reaction notes

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