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

HRID 974171Notes

Reaction equation

HRID 974171 reaction equation
[N:1]1([C@@H:6]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH2:9][CH2:8][C@H:7]2O)[CH2:5][CH2:4][CH2:3][CH2:2]1.CS(Cl)(=O)=O.[CH3:22][NH2:23].[OH-].[Na+]>C(O)C.O.O1CCCC1.C(N(CC)CC)C>[CH3:22][NH:23][C@@H:15]1[C:10]2[C:9](=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:8][CH2:7][C@H:6]1[N:1]1[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

9

Reactant 4

HCID 6329MethylamineHCID 14798Sodium HydroxideHCID 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)naphthalene

Reagents, catalysts & solvents 4

HCID 702EthanolSolvent2×HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8471TriethylamineSolvent

Procedure

A solution of 10.8 g of the product of Step A, 100 ml of tetrahydrofuran and 9.7 ml of triethylamine was cooled to -20° C. and then over 10 minutes, 5.5 ml of methanesulfonyl chloride were added. The precipitate was allowed to return to ambient temperature and then 38 ml of methylamine at 33% in ethanol were added. The mixture was stirred for 20 hours and the tetrahydrofuran and the ethanol were eliminated under reduced pressure at 50° C. 100 ml of water and 10 ml of a solution of sodium hydroxide were added and extraction was done with methylene chloride. The extracts were washed with water, dried, filtered and concentrated to dryness to obtain 11.5 g of the expected product as a brown oil.

Workup

  1. customto return to ambient temperature
  2. customwere eliminated under reduced pressure at 50° C
  3. extractionextraction
  4. washThe extracts were washed with water
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-291a419c503c47b38c49af64c88fcd22
Source dataset
uspto-grants-1991_11
Patent number
US05068244

Reaction notes

Loading…