Water → HCID 13491602, compound

HRID 1284924Notes

Reaction equation

HRID 1284924 reaction equation
[CH:1]([NH:4][CH2:5][CH2:6][C:7]1[C:15]2[C:10](=[C:11]3[CH2:19][N:18]([CH3:20])[CH2:17][CH:16]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[C:12]3=[CH:13][CH:14]=2)[NH:9][CH:8]=1)([CH3:3])[CH3:2].FC(F)(F)C(O)=O.O.[OH-].[Na+]>O1CCCC1>[CH:1]([NH:4][CH2:5][CH2:6][CH:7]1[C:15]2[C:10](=[C:11]3[CH2:19][N:18]([CH3:20])[CH2:17][CH:16]([C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=4)[C:12]3=[CH:13][CH:14]=2)[NH:9][CH2:8]1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 13491616HCID 13491616, compound

Product 1

HCID 13491602HCID 13491602, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2.1 g (0.00604 mol) of 3-(isopropylaminoethyl)-8-methyl-6-phenyl-6,7,8,9-tetrahydro-1H-pyrido[4,3-g]-indole are dissolved in 25 ml (0.3275 mol) of trifluoroacetic acid, with stirring and in the absence of moisture, and a solution of 1.76 g (0.0241 mol) of trimethylaminoborane in 10 ml of tetrahydrofuran is then added dropwise at a temperature of 0°-+2° C. The mixture is subsequently stirred at 0° C. for 1 hour, a solution of 1.76 g (0.0241 mol) of trimethylamonoborane in 10 ml of tetrahydrofuran is then again added and the mixture is subsequently stirred for 2.5 hours. 150 ml of H2O are now added to the reaction mixture, the mixture is brought to pH 13 with NaOH and the oily product which deposits is extracted with CH2Cl2. The CH2Cl2 phase is washed with H2O, dried over Na2SO4 and then freed from the solvent on a rotary evaporator. The residue is chromatographed twice on silica gel (silica gel 60 from E. Merck, Darmstadt). Eluent: initially CH2Cl2 /MeOH/N(C2H5)3 (15:4:0.25), then diethyl ether/MeOH/N(C2H5)3 (15:3:0.25).

Workup

  1. stirringThe mixture is subsequently stirred at 0° C. for 1 hour
  2. stirringthe mixture is subsequently stirred for 2.5 hours
  3. extractionthe oily product which deposits is extracted with CH2Cl2
  4. washThe CH2Cl2 phase is washed with H2O
  5. dry with materialdried over Na2SO4
  6. customfreed from the solvent on a rotary evaporator
  7. customThe residue is chromatographed twice on silica gel (silica gel 60 from E. Merck, Darmstadt)

Sources & evidence

ORD record
ord-d9f2ec4014ca44509c37cbcf014c0b48
Source dataset
uspto-grants-1986_01
Patent number
US04564613

Reaction notes

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