Triethylamine → HCID 19696422, compound

HRID 863693Notes

Reaction equation

HRID 863693 reaction equation
CS(OS(C)(=O)=O)(=O)=O.C([N:12](CC)CC)C.[CH:17]1[CH:25]=[CH:24][CH:23]=[C:22]2[C:18]=1[CH:19]=[C:20]1[CH2:29][CH:28]([CH2:30]O)[CH2:27][CH2:26][N:21]12>ClCCl>[NH2:12][CH2:30][CH:28]1[CH2:27][CH2:26][N:21]2[C:22]3[C:18]([CH:19]=[C:20]2[CH2:29]1)=[CH:17][CH:25]=[CH:24][CH:23]=3

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 81560Methanesulfonic anhydrideHCID 10130409HCID 10130409, compound

Product 1

HCID 19696422HCID 19696422, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

2.4 g of methanesulfonic anhydride and 2 ml of triethylamine were added to a stirred solution of 2.01 g of 6,7,8,9-tetrahydropyrido[1,2-a]indole-8-methanol in 40 ml of dichloromethane under a nitrogen atmosphere. After 18 hours, the mixture was washed with saturated sodium bicarbonate solution, dried and evaporated to an oil. Then, 1.8 g of this oil were dissolved in 10 ml of isopropanol and 5 ml of 33% aqueous ammonia and the mixture was heated to 80° C. for 10 hours. The solvent was removed under reduced pressure and the residue was partitioned between dichloromethane and saturated sodium bicarbonate solution. The organic phase was dried and evaporated to give 1.3 g of 8-aminomethyl-6,7,8,9-tetrahydropyrido[1,2-a]indole of melting point 85°-90° C.

Workup

  1. washthe mixture was washed with saturated sodium bicarbonate solution
  2. customdried
  3. customevaporated to an oil
  4. dissolutionThen, 1.8 g of this oil were dissolved in 10 ml of isopropanol
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was partitioned between dichloromethane and saturated sodium bicarbonate solution
  7. customThe organic phase was dried
  8. customevaporated

Sources & evidence

ORD record
ord-4223f1a63c434a9faadaa7c65c19b2d7
Source dataset
uspto-grants-1998_02
Patent number
US05721245

Reaction notes

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