Cyclopropylamine → HCID 15288859, compound

HRID 488088Notes

Reaction equation

HRID 488088 reaction equation
ClCC([O:5][C:6]1[CH:14]=[CH:13][C:12]2[N:11]([CH3:15])[C:10]3[C:16](=O)[CH2:17][CH2:18][C:9]=3[C:8]=2[CH:7]=1)=O.[CH:20]1([NH2:23])[CH2:22][CH2:21]1>C1(C)C=CC=CC=1.[Ti](Cl)(Cl)(Cl)Cl>[CH:20]1([N:23]=[C:16]2[C:10]3[N:11]([CH3:15])[C:12]4[CH:13]=[CH:14][C:6]([OH:5])=[CH:7][C:8]=4[C:9]=3[CH2:18][CH2:17]2)[CH2:22][CH2:21]1

Participants

5

Reactant 2

HCID 69828CyclopropylamineHCID 19003099HCID 19003099, compound

Product 1

HCID 15288859HCID 15288859, compound

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 1140TolueneSolvent2×

Conditions

Temperature
-100 °C

Procedure

7-Chloroacetyloxy-1,4-dihydro-4-methylcyclopent[b]indol-3(2H)-one (15.0 g) and cyclopropylamine (9.6 g) were dissolved in 300 ml toluene and cooled to -100° C. Titanium tetrachloride (6.3 g) dissolved in 50 ml toluene was added slowly to the first solution. The reaction mixture was allowed to come up to room temperature and stirred overnight. The next day another 1.5 equivalents of the amine (4.6 g) was added to the reaction mixture and the mixture was stir-red for one hour. The reaction mixture was filtered through a pad of silica gel, eluting with 3:1 hexane/ethyl acetate, giving a yellow oil after removal of solvents. 3-Cyclopropylimino-4-methyl-1,2,3,4-tetrahydrocyclopent[b]-indol-7-ol was isolated as a light yellow solid (3.3 g) after flash chromatography and recrystallization from ethyl acetate.

Workup

  1. additionwas added slowly to the first solution
  2. customto come up to room temperature
  3. waitthe mixture was stir-red for one hour
  4. filtrationThe reaction mixture was filtered through a pad of silica gel
  5. washeluting with 3:1 hexane/ethyl acetate
  6. customgiving a yellow oil
  7. customafter removal of solvents

Sources & evidence

ORD record
ord-80f801a384db4b609f30925f8b7252e7
Source dataset
uspto-grants-1994_03
Patent number
US05298626

Reaction notes

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