Triethylamine → trans-1,2,3,4-Tetrahydro-1-methylamino-2-(pyrrolidin-1-yl)naphthalene

HRID 1085481Notes

Reaction equation

HRID 1085481 reaction equation
CS(Cl)(=O)=O.O[C@@H:7]1[CH2:16][CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C@H:8]1[N:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1.[CH2:22]([N:24](CC)CC)C>C(Cl)Cl>[CH3:22][NH:24][C@@H:9]1[C:14]2[C:15](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:16][CH2:7][C@H:8]1[N:17]1[CH2:18][CH2:19][CH2:20][CH2:21]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 14476580trans-1,2,3,4-Tetrahydro-2-hydroxy-1-(pyrrolidin-1-yl)naphthalene

Product 1

HCID 14476583trans-1,2,3,4-Tetrahydro-1-methylamino-2-(pyrrolidin-1-yl)naphthaleneYield 56.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of methanesulfonyl chloride (10.3 g) in methylene chloride (50 ml) was added rapidly in drops to a stirred and cooled (0.5° C.) solution of trans-1,2,3,4-tetrahydro-2-hydroxy-1-(pyrrolidin-1yl)naphthalene (10.3 g) and triethylamine (10 g) in methylene chloride (100 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 carefully with a 33% solution of methylamine in ethanol (125 ml) and the mixture was stirred at reflux for 2 hours followed by evaporation of the solvent under reduced pressure. The residue was treated with water and extracted twice with ether. The combined ether extracts were washed with 2N sodium hydroxide and then with water, dried over magnesium sulfate and evaporated under reduced pressure. The residual viscous liquid was distilled under vacuum to yield trans-1,2,3,4-tetrahydro-1-methylamino-2-(pyrrolidin-1-yl)naphthalene (6.2 g), b.p. 126°-134°/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 carefully with a 33% solution of methylamine in ethanol (125 ml)
  5. stirringthe mixture was stirred
  6. temperatureat reflux for 2 hours
  7. customfollowed by evaporation of the solvent under reduced pressure
  8. additionThe residue was treated with water
  9. extractionextracted twice with ether
  10. washThe combined ether extracts were washed with 2N sodium hydroxide
  11. dry with materialwith water, dried over magnesium sulfate
  12. customevaporated under reduced pressure
  13. distillationThe residual viscous liquid was distilled under vacuum

Sources & evidence

ORD record
ord-a83ed248717f4c279761d4fe0da2e6b9
Source dataset
uspto-grants-1991_04
Patent number
US05010085

Reaction notes

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