1'-Acetyl-5,6-dihydrospiro[1H-indolo[3,2-c]quinoline-6,4'-piperidine] → 1'-Ethyl-5,6-dihydrospiro[1H-indolo[3,2-c]quinoline-6,4'-piperidine]

HRID 1084722Notes

Reaction equation

HRID 1084722 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][C:7]2([C:18]3=[C:19]4[C:24](=[N:25][C:17]3=[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH2:15]3)[NH:10]2)[CH:23]=[CH:22][CH:21]=[CH:20]4)[CH2:6][CH2:5]1)(=O)[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3].C1COCC1>C1COCC1.CO.C(Cl)Cl>[CH2:1]([N:4]1[CH2:5][CH2:6][C:7]2([C:18]3=[C:19]4[C:24](=[N:25][C:17]3=[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH2:15]3)[NH:10]2)[CH:23]=[CH:22][CH:21]=[CH:20]4)[CH2:8][CH2:9]1)[CH3:2]

Participants

5

Reactant 2

HCID 198249201'-Acetyl-5,6-dihydrospiro[1H-indolo[3,2-c]quinoline-6,4'-piperidine]HCID 68718528lithium aluminium hydride THF

Product 1

HCID 198249211'-Ethyl-5,6-dihydrospiro[1H-indolo[3,2-c]quinoline-6,4'-piperidine]Yield 48.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

A solution of 7.5 g of 1'-acetyl-5,6-dihydrospiro-[1H-indolo-[3,2-c]quinoline-6,4'-piperidine] in 60 ml of THF was added dropwise to 45 ml of 1M LiAlH4 /THF. The solution was stirred at room temperature for 30 minutes and thereafter quenched with NH4Cl, filtered through celite and concentrated to give 9.2 g of crude product. Flash chromatography using 7% CH3OH/CH2Cl2 as an eluent gave 3.5 g of solid, m.p. 238°-240° dec.

Workup

  1. customquenched with NH4Cl
  2. filtrationfiltered through celite and
  3. concentrationconcentrated
  4. customto give 9.2 g of crude product

Sources & evidence

ORD record
ord-9b14695587964b01bb08ee76976671a9
Source dataset
uspto-grants-1991_04
Patent number
US05006531

Reaction notes

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