Triethylamine → HCID 66898674, compound

HRID 1465035Notes

Reaction equation

HRID 1465035 reaction equation
C(N(CC)CC)C.BrCC[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1.Cl.[C:20]1([CH3:28])[CH:25]=[CH:24][C:23]([NH:26][NH2:27])=[CH:22][CH:21]=1>C(O)C>[CH3:18][O:17][C:14]1[CH:13]=[CH:12][C:11]([N:26]([C:23]2[CH:24]=[CH:25][C:20]([CH3:28])=[CH:21][CH:22]=2)[NH2:27])=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 125044-Methylphenylhydrazine monohydrochlorideHCID 844271-(2-Bromoethyl)-4-methoxybenzene

Product 1

HCID 66898674HCID 66898674, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Triethylamine (5.2 mL 37.8 mmol) and (1-(2-Bromoethyl)-4-methoxybenzene (1.9 mL, 12.60 mmol) were added to a solution of p-tolylhydrazine hydrochloride (2 gm, 12.60 mmol) in ethanol (30 mL) and the resulting solution was stirred at RT for an 1 h after which it was heated at 90° C. for 2-3 h. The reaction mixture was concentrated to dryness and basified with aq. saturated NaHCO3, and extracted in ethyl acetate. The combined organic layers was dried over Na2SO4 and concentrated to obtain (1-(4-methoxyphenyl)-1-p-tolylhydrazine (2.8 g). (1-(4-methoxyphenyl)-1-p-tolylhydrazine (2.8 g, 10.9 mmol) and 8-methyl-8-azabicyclo[3.2.1]octan-3-one (1.5 gm, 10.9 mmol) were taken in ethanolic HCl (30 mL), and stirred at RT for 15 min and the solvent was removed in vacuo. The residue was taken in ethanol (30 mL) and heated at 90° C. for 3. After completion of the reaction (the progress of the reaction was monitored by LCMS), the reaction mixture was concentrated to dryness and basified with aq. saturated NaHCO3. The product was extracted in ethyl acetate and the organic layers were separated, dried over Na2SO4 and concentrated. The resulting crude product was purified over neutral alumina (10% Me-OH in dichloromethane) to obtain the product as free base (500 mg). The NMR data for the compound is as follows: 1H NMR (DMSO)—7.40-7.35 (d, 1H), 7.25 (s, 1H), 6.90-6.85 (d, 1H), 6.85-6.80 (d, 2H), 6.80-6.75 (d, 2H), 4.25-4.10 (t, 2H), 3.85-3.75 (m, 1H), 3.65 (s, 3H), 3.00-2.80 (t, 2H), 2.65-2.55 (d, 2H), 2.30 (s, 3H), 2.20-2.00 (m, 1H), 1.95 (s, 3H), 1.45-1.40 (m, 2H), 1.40-1.35 (m, 2H).

Workup

  1. temperaturewas heated at 90° C. for 2-3 h
  2. concentrationThe reaction mixture was concentrated to dryness
  3. extractionextracted in ethyl acetate
  4. dry with materialThe combined organic layers was dried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-23b68646303246febb1e8b45468cdcec
Source dataset
uspto-grants-2015_04
Patent number
US08999977B2

Reaction notes

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