Hydrochloric Acid → HCID 20353247, compound

HRID 372100Notes

Reaction equation

HRID 372100 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5](Cl)(=[O:7])[CH3:6].[CH:9]1([CH2:14][N:15]2[CH2:19][C:18]34[CH2:29][CH:22]([C:23]5[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=5[CH:17]3[CH2:16]2)[C:21]2[CH:30]=[CH:31][CH:32]=[CH:33][C:20]4=2)[CH2:13][CH2:12][CH2:11][CH2:10]1.Cl>C(Cl)Cl>[C:5]([C:32]1[CH:31]=[CH:30][C:21]2[CH:22]3[CH2:29][C:18]4([CH2:19][N:15]([CH2:14][CH:9]5[CH2:13][CH2:12][CH2:11][CH2:10]5)[CH2:16][CH:17]4[C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=43)[C:20]=2[CH:33]=1)(=[O:7])[CH3:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 12621149HCID 12621149, compound

Product 1

HCID 20353247HCID 20353247, compoundYield 110%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 5.0 g (37.39 mmoles) of aluminum chloride in 75 ml of methylene chloride, cooled to 0°, was added dropwise 3.0 g (38.2 mmoles) of acetyl chloride. Then 5.0 g (13.7 mmoles) of 2-cyclopentylmethyl-2,3,8,12b-tetrahydro1H-3a,8methanodibenzo[3,4:6,7]cyclohepta[1,2-c]pyrrole was added portionwise. The reaction mixture was heated at reflux for several hours and then poured into 1N aqueous hydrochloric acid. The product was extracted with methylene chloride, and the extracts were washed with water, with 1N aqueous sodium hydroxide, with water and dried over potassium carbonate. The solvent was evaporated to leave 5.6 g of 5-acetyl-2-cyclopentylmethyl-2,3,8,12b-tetrahydro-1H-3a,8-methanodibenzo[3,4:6,7]cyclohepta[1,2-c]pyrrole as an oil; nmr spectrum: δ 1.0-4.0 (m, 19); 2.5 (s, 3); 7.1-7.25 (m, 5); 7.7-7.9 (m, 2). The 220MHz nmr spectrum showed that the product contained approximately 83% of the 5-acetyl isomer. A sample was purified by crystallization of the trifluoroacetate salt from ether/ethyl acetate and then of the hydrochloride salt from acetone, mp, 160-172° (dec.); ir. 1700 cm-1 (COCH3).

Workup

  1. temperaturecooled to 0°
  2. temperatureThe reaction mixture was heated
  3. temperatureat reflux for several hours
  4. extractionThe product was extracted with methylene chloride
  5. washthe extracts were washed with water, with 1N aqueous sodium hydroxide, with water
  6. dry with materialdried over potassium carbonate
  7. customThe solvent was evaporated

Sources & evidence

ORD record
ord-e28c88ad0eaf4e16b4d8fee7e62a2abc
Source dataset
uspto-grants-1978_05
Patent number
US04088772

Reaction notes

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