Potassium Carbonate → Quinolizidin-2-ylmethyl-3,4-dihydro-2 H-[1,3]oxazino[3,2-a]indole-10-Carboxylate

HRID 1458596Notes

Reaction equation

HRID 1458596 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[CH2:23][CH2:22][N:21]3[CH:16]([CH2:17][CH2:18][CH2:19][CH2:20]3)[CH2:15]2)=[O:11])=[CH:2]1.ClN1[C:29](=[O:30])[CH2:28][CH2:27]C1=O.BrCCCO.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:15]1[CH:16]2[N:21]([CH2:20][CH2:19][CH2:18][CH2:17]2)[CH2:22][CH2:23][CH:14]1[CH2:13][O:12][C:10]([C:3]1[C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:9]=2[N:1]2[CH2:27][CH2:28][CH2:29][O:30][C:2]=12)=[O:11]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 123083-Bromo-1-propanolHCID 31398ChlorosuccinimideHCID 131719520Quinolizidin-2-ylmethylindole-3-carboxylate

Product 1

HCID 44211268Quinolizidin-2-ylmethyl-3,4-dihydro-2 H-[1,3]oxazino[3,2-a]indole-10-CarboxylateYield 51%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

eq-Quinolizidin-2-ylmethyl 1 H-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 using the same chromatography conditions as in Example 1b to afford the title compound as a colourless oil (51%). This was converted to its hydrochloride salt and crystallised from acetone mp 164°-167° C.

Workup

  1. customThe crude product was purified

Sources & evidence

ORD record
ord-8864d76f566143bd9313b36a6b487eca
Source dataset
uspto-grants-1998_12
Patent number
US05852014

Reaction notes

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