1,2-Ethanediamine, N1-phenyl- → HCID 178516055, compound

HRID 896643Notes

Reaction equation

HRID 896643 reaction equation
O[C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[C:15]1([NH:21][CH2:22][CH2:23][NH2:24])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[BH4-].[Na+]>CC(O)C.C1COCC1>[C:15]1([NH:21][CH2:22][CH2:23][NH:24][C@H:2]2[CH2:7][CH2:6][C@H:5]([C:8]3[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=3)[CH2:4][CH2:3]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 742701,2-Ethanediamine, N1-phenyl-HCID 4311764Sodium borohydrideHCID 45989164-(4'-Hydroxyphenyl)cyclohexanone

Product 1

HCID 178516055HCID 178516055, compoundYield 18.8%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 4-(4-hydroxyphenyl)cyclohexanone (1.0 g, 5.3 mmol) in a mixture of 2-propanol (40 mL) and THF (20 mL) was added N-phenylethylenediamine (0.72 g, 5.3 mmol) and 3 Å molecular sieves. After 3 hours, sodium borohydride (0.27 g, 7.3 mmol) was added, and the reaction mixture was stirred overnight. The reaction mixture was quenched with MeOH, filtered through celite, and the filtrate was concentrated under reduced pressure. The product was purified by flash chromatography (silica, 95:5 CH2Cl2:MeOH) and converted to a maleate salt. Recrystallization from MeOH/Et2O gave trans-4-[4-(2-phenylamino-ethylamino)cyclohexyl]phenol (0.31 g, 14%), as yellow solid: mp 180-184° C.; IR (KBr): 3368, 2945, 2863, 1516 cm−1; 1H NMR (500 MHz, DMSO-d6) δ 9.14 (s, 1H), 8.40 (br s, 2H), 7.15-7.00 (m, 4H), 6.70-6.55 (m, 5H), 6.02 (s, 2H), 5.65 (br s, 1H), 3.40-3.25 (m, 2H), 3.20-3.10 (m, 3H), 2.45-2.40 (m, 1H), 2.20-2.10 (m, 2H), 1.90-1.80 (m, 2H), 1.50-1.35 (m, 4H); API-MS (m/z): 311 [M+H]+; HPLC: method A, 7.38 minutes (99.1%); method B, 13.29 minutes (99.1%); Anal. Calcd for C20H26N2O.C4H4O4: C, 67.59; H, 7.09; N, 6.57. Found: C, 67.38; H, 7.01; N 6.55.

Workup

  1. customThe reaction mixture was quenched with MeOH
  2. filtrationfiltered through celite
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe product was purified by flash chromatography (silica, 95:5 CH2Cl2:MeOH)
  5. customRecrystallization from MeOH/Et2O

Sources & evidence

ORD record
ord-bae92b5afe5a4dc08c7cf0f1c55432a8
Source dataset
uspto-grants-2005_07
Patent number
US06919377B2

Reaction notes

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