Acetyl chloride → HCID 178475030, compound

HRID 1756535Notes

Reaction equation

HRID 1756535 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9]([C@@H:11]2[CH2:25][C@H:24]3[C@@H:14]([CH2:15][C:16]4[C:26]5[C:19](=[CH:20][CH:21]=[CH:22][C:23]3=5)[N:18]([CH:27]([CH3:29])[CH3:28])[CH:17]=4)[N:13]([CH3:30])[CH2:12]2)=[O:10])[CH2:4][CH2:3]1.C(N(CC)CC)C.[C:38](Cl)(=[O:40])[CH3:39]>O1CCCC1>[C:38]([NH:1][C@H:2]1[CH2:3][CH2:4][C@H:5]([NH:8][C:9]([C@@H:11]2[CH2:25][C@H:24]3[C@@H:14]([CH2:15][C:16]4[C:26]5[C:19](=[CH:20][CH:21]=[CH:22][C:23]3=5)[N:18]([CH:27]([CH3:28])[CH3:29])[CH:17]=4)[N:13]([CH3:30])[CH2:12]2)=[O:10])[CH2:6][CH2:7]1)(=[O:40])[CH3:39]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 178456165HCID 178456165, compound

Product 1

HCID 178475030HCID 178475030, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 620 mg of (8β)-N-(trans-4-aminocyclohexyl)-1-isopropyl-6-methylergoline-8-carboxamide in 100 ml of dry tetrahydrofuran were added 222 μl of triethylamine. The solution was cooled by means of an external ice bath and 118 μl of acetyl chloride were added in dropwise fashion. The mixture was stirred at room temperature under a nitrogen atmosphere for 2.5 hours. The reaction mixture was concentrated in vacuo and ethyl acetate, water, and 2N sodium hydroxide were added. The layers were separated and the aqueous layer extracted an additional three times with ethyl acetate and six times with methylene chloride. The combined organic layers were washed twice with water, once with a saturated sodium chloride solution, dried over sodium sulfate and concentrated in vacuo to provide 690 mg of a pale yellow solid. This material was crystallized from tetrahydrofuran/ethanol/hexanes to provide 259 mg of title product as a tan powder, m.p. >280° C. Analytical high pressure liquid chromatography indicated the material was 97.9% pure. NMR, MS

Workup

  1. temperatureThe solution was cooled by means of an external ice bath
  2. concentrationThe reaction mixture was concentrated in vacuo and ethyl acetate, water, and 2N sodium hydroxide
  3. additionwere added
  4. customThe layers were separated
  5. extractionthe aqueous layer extracted an additional three times with ethyl acetate and six times with methylene chloride
  6. washThe combined organic layers were washed twice with water, once with a saturated sodium chloride solution
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d06a0ee6674049158b7ab7fb7a63326e
Source dataset
uspto-grants-1995_08
Patent number
US05441961

Reaction notes

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