1,1,3,3-Tetramethylguanidine → HCID 18951361, compound

HRID 1492696Notes

Reaction equation

HRID 1492696 reaction equation
C(O[CH:5]1[C:10]2=[CH:11][C:12]3[C:17]([N:9]2[CH2:8][CH2:7][CH:6]1[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:16][CH:15]=[CH:14][CH:13]=3)(=O)C.CN(C)C(N(C)C)=N>C1(C)C=CC=CC=1>[CH:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:12]=1[CH:11]=[C:10]1[CH:5]=[C:6]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:7][CH2:8][N:9]12

Participants

4

Reactant 2

HCID 664601,1,3,3-TetramethylguanidineHCID 18951359HCID 18951359, compound

Product 1

HCID 18951361HCID 18951361, compoundYield 83.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 9.93 g (0.033 mol) of ethyl 9-acetoxy-6,7,8,9-tetrahydropyrido[1,2-a]indole-8-carboxylate in 150 ml of toluene is treated with 8.3 ml (0.066 mol) of 1,1,3,3-tetra-methylguanidine and the reaction mixture is heated at 80° C. for 17 hours. The resulting solution is then cooled to room temperature, washed in succession three times with 50 ml of 1N hydrochloric acid each time, 50 ml of aqueous sodium bicarbonate solution and 50 ml of sodium chloride solution, dried over anhydrous sodium sulfate and evaporated to dryness. After trituration of the residue with n-hexane, there are obtained 6.64 g (83%) of ethyl 6,7-dihydropyrido[1,2-a]indole-8-carboxylate as a pale yellow solid, m.p. 77°-79° C.

Workup

  1. temperatureThe resulting solution is then cooled to room temperature
  2. washwashed in succession three times with 50 ml of 1N hydrochloric acid each time, 50 ml of aqueous sodium bicarbonate solution and 50 ml of sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-b11a828771ad45b8856117e1175a3bf2
Source dataset
uspto-grants-1994_12
Patent number
US05374727

Reaction notes

Loading…