Acetyl chloride → HCID 20353268, compound

HRID 372099Notes

Reaction equation

HRID 372099 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:20]3[CH2:21][C:7]4([CH2:11][N:10]([CH2:12][CH:13]5[CH2:17][CH2:16][CH2:15][CH2:14]5)[CH2:9][CH:8]4[C:18]4[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=43)[C:6]=2[CH:26]=1.C(N(CC)CC)C.[C:34](Cl)(=[O:36])[CH3:35].[OH-].[Na+]>C(Cl)(Cl)Cl>[C:34]([NH:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:20]3[CH2:21][C:7]4([CH2:11][N:10]([CH2:12][CH:13]5[CH2:14][CH2:15][CH2:16][CH2:17]5)[CH2:9][CH:8]4[C:18]4[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=43)[C:6]=2[CH:26]=1)(=[O:36])[CH3:35]

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 20353202HCID 20353202, compound

Product 1

HCID 20353268HCID 20353268, compoundYield 38.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 3.0 g (8.7 mmoles) of 5amino-2-cyclopentylmethyl-2,3,8,12b-tetrahydro-1H-3a, 8-methanodibenzo[3,4:6,7]cyclohepta[1,2-c]pyrrole and 10 ml of triethylamine in 25 ml of chloroform, cooled to 0°, was added dropwise 2.5 g (31.8 mmoles) of acetyl chloride. The reaction mixture was stirred overnight at room temperature and then for 30 minutes with 2.5 N aqueous sodium hydroxide. The organic layer was separated and the aqueous layer was extracted with methylene chloride. The combined organic extracts were washed with water, dried over potassium carbonate, and concentrated under vacuum. The residue was chromatographed on silica gel CC No. 7 with 57% methanol in chloroform to give 1.3 g of 5-acetamido-2-cyclopentylmethyl- 2,3,8,12b-tetrahydro1H-3a,8-methanodibenzo[3,4:6,7]cyclohepta[1,2-c]pyrrole as an oil; nmr spectrum: δ 1.0-4.0 (m, 19); 2.1 (s, 3); 6.8-7.8 (m, 7).

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted with methylene chloride
  3. washThe combined organic extracts were washed with water
  4. dry with materialdried over potassium carbonate
  5. concentrationconcentrated under vacuum
  6. customThe residue was chromatographed on silica gel CC No

Sources & evidence

ORD record
ord-6c039bde23a64ea3a7e29949c0379f75
Source dataset
uspto-grants-1978_05
Patent number
US04088772

Reaction notes

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