Triethylamine → HCID 14126789, compound

HRID 1651609Notes

Reaction equation

HRID 1651609 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 2 N 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 2 N 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-52d5992060614776b21b673cf5cc5650
Source dataset
uspto-grants-1990_05
Patent number
US04929627

Reaction notes

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