Ammonium Chloride → HCID 131718483, compound

HRID 1109145Notes

Reaction equation

HRID 1109145 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][C:9]1[C:21]2[CH2:20][CH2:19][C@H:18]3[C@H:14]([CH2:15][C:16](=O)[N:17]3[CH2:22][CH2:23][N:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)[C:13]=2[CH:12]=[CH:11][CH:10]=1.[NH4+].[Cl-]>C1COCC1>[CH3:7][O:8][C:9]1[C:21]2[CH2:20][CH2:19][C@H:18]3[C@H:14]([CH2:15][CH2:16][N:17]3[CH2:22][CH2:23][N:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)[C:13]=2[CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 21226445Aluminium lithium hydrideHCID 131718482HCID 131718482, compound

Product 1

HCID 131718483HCID 131718483, compoundYield 90.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1.0 g (0.0268 mol) of lithium aluminum hydride was suspended in 50 ml of THF under argon. A solution of 4.4 g (0.0134 mol) of rac-cis-1,3,3a,4,5,9b-hexahydro-6-methoxy-3-(2-piperidinoethyl)-2H-benzo[e]indol-2-one in 100 ml of THF was added dropwise thereto and the mixture was boiled under reflux for 1 hour. 25 ml of a saturated aqueous NH4Cl solution was cautiously added dropwise thereto, the mixture was filtered and the filtrate was extracted with ethyl acetate. The organic phase was washed with water, dried with MgSO4, filtered and concentrated. There were obtained 3.8 g (90%) of rac-cis-2,3,3a,4,5,9b-hexahydro-6-methoxy-3-(2-piperidinoethyl)-1H-benzo[e]indole as a colorless oil.

Workup

  1. temperatureunder reflux for 1 hour
  2. filtrationthe mixture was filtered
  3. extractionthe filtrate was extracted with ethyl acetate
  4. washThe organic phase was washed with water
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-353ca765afa64f2391fe42ab4027d547
Source dataset
uspto-grants-1994_06
Patent number
US05318966

Reaction notes

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