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

HRID 609589Notes

Reaction equation

HRID 609589 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 1H-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-885c588d88e04b878be427c1126e6346
Source dataset
uspto-grants-1999_12
Patent number
US05998409

Reaction notes

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