Triethylamine → HCID 14126789, compound

HRID 2352293Notes

Reaction equation

HRID 2352293 reaction equation
CS(Cl)(=O)=O.O[C@@H:7]1[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C@H:8]1[N:16]1[CH2:20][CH2:19][CH2:18][CH2:17]1.[CH2:21]([N:23](CC)CC)C>C(Cl)Cl>[CH3:21][NH:23][C@@H:9]1[C:14]2[C:15](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:7][C@H:8]1[N:16]1[CH2:17][CH2:18][CH2:19][CH2:20]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 14126784HCID 14126784, compound

Product 1

HCID 14126789HCID 14126789, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of methanesulfonyl chloride (6 g) in methylene chloride (50 ml) was added dropwise rapidly to a stirred and cooled (0°-5°) solution of trans-2,3-dihydro-2-hydroxy-(pyrrolidin-1-yl)-1H-indene (5.5 g) and triethylamine (6 ml) in methylene chloride (200 ml). After the addition was complete, the mixture was stirred at room temperature for 3 hours and then evaporated under reduced pressure. The residue was treated with a 33% solution of methylamine in ethanol (100 ml) and the mixture was stirred at reflux for 3 hours and evaporated under reduced pressure. The residue was treated with water and extracted twice with ether. The combined ether extracts were washed successively with 2N sodium hydroxide solution and water, dried over magnesium sulfate and evaporated under reduced pressure to yield a liquid which was distilled under vacuum to give trans-2,3-dihydro-1-methylamino-2-(pyrrolidin-1-yl)-1H-indene (6.3 g) b.p. 118°-120°/0.25 torr.

Workup

  1. additionAfter the addition
  2. stirringthe mixture was stirred at room temperature for 3 hours
  3. customevaporated under reduced pressure
  4. additionThe residue was treated with a 33% solution of methylamine in ethanol (100 ml)
  5. stirringthe mixture was stirred
  6. temperatureat reflux for 3 hours
  7. customevaporated under reduced pressure
  8. additionThe residue was treated with water
  9. extractionextracted twice with ether
  10. washThe combined ether extracts were washed successively with 2N sodium hydroxide solution and water
  11. dry with materialdried over magnesium sulfate
  12. customevaporated under reduced pressure
  13. customto yield a liquid which
  14. distillationwas distilled under vacuum

Sources & evidence

ORD record
ord-86060715b49345eeb4a3eaa822d4dd4a
Source dataset
uspto-grants-1989_10
Patent number
US04876269

Reaction notes

Loading…