Potassium Carbonate → (1-Benzyl-4-piperidyl)methyl-3,4-dihydro-2H-[1,3]oxazino[3,2-a]indole-10-carboxylate

HRID 609594

Reaction equation

HRID 609594 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([O:12][CH2:13][CH:14]2[CH2:19][CH2:18][N:17]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:16][CH2:15]2)=[O:11])=[CH:2]1.ClN1[C:32](=[O:33])[CH2:31][CH2:30]C1=O.BrCCCO.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:20]([N:17]1[CH2:18][CH2:19][CH:14]([CH2:13][O:12][C:10]([C:3]2[C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:9]=3[N:1]3[CH2:30][CH2:31][CH2:32][O:33][C:2]=23)=[O:11])[CH2:15][CH2:16]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 123083-Bromo-1-propanolHCID 31398ChlorosuccinimideHCID 19599412(1-Benzyl-4-piperidyl)methyl indole-3-carboxylate

Product 1

HCID 44211270(1-Benzyl-4-piperidyl)methyl-3,4-dihydro-2H-[1,3]oxazino[3,2-a]indole-10-carboxylate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

(1-Benzyl-4-piperidyl)methyl indole-3-carboxylate was treated initially with N-chlorosuccinimide (1.5 equivalents) for 2 h, then with 3-bromo-1-propanol (2 equivalents) for 16 h, followed by anhydrous potassium carbonate in acetone, using the method described in Example 1b. The crude product was purified by chromatography on silica gel eluting with chloroform/ethanol (19:1) to afford the title compound (E15) as a beige solid following recrystallisation from chloroform/ether (47%) mp 158-160° C.

Workup

  1. customThe crude product was purified by chromatography on silica gel eluting with chloroform/ethanol (19:1)

Sources & evidence

ORD record
ord-5521d219a792422d840f0871131d7381
Source dataset
uspto-grants-1999_12
Patent number
US05998409

Linked notes

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