4-Phenylpiperidinium chloride → HCID 24803652, compound

HRID 409562Notes

Reaction equation

HRID 409562 reaction equation
Cl.[C:2]1([CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:14]=[C:15]1[N:20]([CH2:21][CH:22]=O)[C:19]2[CH:24]=[CH:25][CH:26]=[CH:27][C:18]=2[O:17][CH2:16]1>C(O)C.C(Cl)Cl>[C:2]1([CH:8]2[CH2:9][CH2:10][N:11]([CH2:22][CH2:21][N:20]3[C:19]4[CH:24]=[CH:25][CH:26]=[CH:27][C:18]=4[O:17][CH2:16][C:15]3=[O:14])[CH2:12][CH2:13]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 825094-Phenylpiperidinium chlorideHCID 509908121000771-62-9

Product 1

HCID 24803652HCID 24803652, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

Following the procedure of Synthetic Comm. 23 (6), 789-795, 1993, to a solution of 4-phenylpiperidine hydrochloride Compound 1-9 (290 mg, 1.5 mmol) and Compound 1-4 (300 mg, 1.5 mmol) in 10 mL of absolute ethanol was added BAP (154 μL, 1.5 mmol). After stirring for 2 hrs, an additional equivalent of aldehyde Compound 1-4 and BAP was added. The reaction mixture was stirred overnight and concentrated to give an oily residue. The residue was taken up in DCM, washed with saturated sodium bicarbonate solution NaHCO3 and brine, dried over Na2SO4, and concentrated. The residue was purified on silica gel (elution with 30% EtOAc in hexane) to yield Compound 86 as a glass-like oil (287 mg, 57%) of a glass-like oil. 1H NMR (300 MHz, CDCl3) δ 7.25-7.11 (m, 5H), 7.04-6.91 (m, 4H), 4.53 (s, 2H), 4.04 (m, 2H), 3.04 (m, 2H), 2.58 (m, 2H), 2.45-2.40 (m, 1H), 2.15, (t of d, J=11 and 3 Hz, 2H), 1.83-1.64 (m, 4H); MS (ES+) m/z 337.2 (M+1); Anal Calcd. for C21H24N2O2.0.51H2O: C, 73.02; H, 7.29; N, 8.11. Found: C, 72.98; H, 7.11; N, 8.00.

Workup

  1. stirringThe reaction mixture was stirred overnight
  2. concentrationconcentrated
  3. customto give an oily residue
  4. washwashed with saturated sodium bicarbonate solution NaHCO3 and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified on silica gel (elution with 30% EtOAc in hexane)

Sources & evidence

ORD record
ord-e769bbecee184e93aec1c2e5200c80ec
Source dataset
uspto-grants-2014_06
Patent number
US08759342B2

Reaction notes

Loading…