Pyridine → HCID 19045318, compound

HRID 1781389Notes

Reaction equation

HRID 1781389 reaction equation
[CH3:1][S:2]([NH:5][C:6]1[CH:7]=[CH:8][C:9]2[O:28][C:13]3([CH2:18][CH2:17][N:16]([CH2:19][CH2:20][C:21]4[CH:26]=[CH:25][C:24]([NH2:27])=[CH:23][CH:22]=4)[CH2:15][CH2:14]3)[CH2:12][C:11](=[O:29])[C:10]=2[CH:30]=1)(=[O:4])=[O:3].N1C=CC=CC=1.[C:37](Cl)(=[O:39])[CH3:38]>C(Cl)Cl>[CH3:1][S:2]([NH:5][C:6]1[CH:7]=[CH:8][C:9]2[O:28][C:13]3([CH2:18][CH2:17][N:16]([CH2:19][CH2:20][C:21]4[CH:22]=[CH:23][C:24]([NH:27][C:37](=[O:39])[CH3:38])=[CH:25][CH:26]=4)[CH2:15][CH2:14]3)[CH2:12][C:11](=[O:29])[C:10]=2[CH:30]=1)(=[O:3])=[O:4]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 19045412HCID 19045412, compound

Product 1

HCID 19045318HCID 19045318, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of 6-methanesulfonamido-3,4-dihydro-1'-(2-(4-aminophenyl)ethyl)-spiro[(2H)-1-benzopyran-2,4'-piperidine]-4-one (0.50 g, 1.2 mmol), and pyridine (0.09 mL, 1.2 mmol) in 25 mL of methylene chloride was cooled in an ice bath and treated dropwise with acetyl chloride (0.09 mL, 1.2 mmol). The mixture was stirred at 0° C. for 2 hours, and then filtered. The tan solid was washed with methylene chloride and dried in the air. The solid was found to be a mixture by thin layer analysis, and was chromatographed on silica gel using 10% methanol in methylene chloride eluant. The pure oil was dissolved in 20 mL of absolute ethanol and was treated with excess 4.8N ethanolic HCl. The solution was then concentrated to 10 mL. The resulting ivory colored solid was collected, washed with diethyl ether, and dried 3 hours at 100° C. under vacuum to give 0.10 g (18%) of product, mp 294° C. (dec).

Workup

  1. temperaturewas cooled in an ice bath
  2. filtrationfiltered
  3. washThe tan solid was washed with methylene chloride
  4. customdried in the air
  5. customwas chromatographed on silica gel using 10% methanol in methylene chloride eluant
  6. dissolutionThe pure oil was dissolved in 20 mL of absolute ethanol
  7. additionwas treated with excess 4.8N ethanolic HCl
  8. concentrationThe solution was then concentrated to 10 mL
  9. customThe resulting ivory colored solid was collected
  10. washwashed with diethyl ether
  11. customdried 3 hours at 100° C. under vacuum

Sources & evidence

ORD record
ord-525f17d072ad44f5b9d585107ba4daf9
Source dataset
uspto-grants-1997_05
Patent number
US05633247

Reaction notes

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