Dichloromethane → HCID 86735703, compound

HRID 372104Notes

Reaction equation

HRID 372104 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[CH:22]3[CH2:23][C:9]4([CH2:13][N:12]([CH2:14][CH:15]5[CH2:19][CH2:18][CH2:17][CH2:16]5)[CH2:11][CH:10]4[C:20]4[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=43)[C:8]=2[CH:28]=1)(=O)[CH3:2].Cl.[NH2:30][OH:31].[OH-].[Na+].C(Cl)Cl>C(O)C.O>[C:1](=[N:30][OH:31])([C:4]1[CH:5]=[CH:6][C:7]2[CH:22]3[CH2:23][C:9]4([CH2:13][N:12]([CH2:14][CH:15]5[CH2:19][CH2:18][CH2:17][CH2:16]5)[CH2:11][CH:10]4[C:20]4[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=43)[C:8]=2[CH:28]=1)[CH3:2]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 20353247HCID 20353247, compound

Product 1

HCID 86735703HCID 86735703, compoundYield 24.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

To a stirred mixture of 5.0 g (13.6 mmoles) of 5-acetyl-2-cyclopentylmethyl-2,3,8,12b-tetrahydro-1H-3a,8-methanodibenzo[3,4:6,7]cyclohepta[1,2-c]pyrrole, (Example 66), and 1.5 g (21.3 mmoles) of hydroxylamine hydrochloride in 25 ml of ethanol and 5.0 ml of water was added portionwise 2.8 g (70 mmoles) of powdered sodium hydroxide. The reaction mixture was then heated at reflux for 5 minutes, cooled, and distributed between water and methylene chloride. The organic layer was washed with water, dried over sodium sulfate and evaporated. The residue was chromatographed on silica gel CC No. 7 with 5% methanol in chloroform to give 1.3 g of 5-acetyl-2-cyclopentylmethyl-2,3,8,12b-tetrahydro-1H-3a,8-methanodibenzo[3,4:6,7]cyclohepta[1,2-c]pyrrole oxime as an oil; nmr spectrum: δ 1.0-4.0 (m, 19); 2.2 (s, 2); 6.8-7.4 (m, 7); 7.5 (s, 1).

Workup

  1. temperatureThe reaction mixture was then heated
  2. temperatureat reflux for 5 minutes
  3. temperaturecooled
  4. washThe organic layer was washed with water
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customThe residue was chromatographed on silica gel CC No

Sources & evidence

ORD record
ord-5d222abcdad240968f7853e342f5ec99
Source dataset
uspto-grants-1978_05
Patent number
US04088772

Reaction notes

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