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

HRID 1458597Notes

Reaction equation

HRID 1458597 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][CH2:14][N:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)=[O:11])=[CH:2]1.ClN1[C:26](=[O:27])[CH2:25][CH2:24]C1=O.BrCCCO.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[O:27]1[C:2]2=[C:3]([C:10]([O:12][CH2:13][CH2:14][N:15]3[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]3)=[O:11])[C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:9]=3[N:1]2[CH2:24][CH2:25][CH2:26]1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 123083-Bromo-1-propanolHCID 31398ChlorosuccinimideHCID 3272300SB 203186

Product 1

HCID 195994092-(1-Piperidyl)ethyl 3,4-dihydro-2H-[1,3]oxazino[3,2-a]indole-10-carboxylate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-(1-Piperidyl)ethyl 1 H-indole-3-carboxylate was treated initially with N-chlorosuccinimide (1.5 equivalents) for 2 h, then with 3-bromo-1-propanol (3 equivalents) for 21 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. (E4) as a pale yellow oil (15%). This was converted to its oxalate salt and crystallised from acetone mp 174°-177° C.

Workup

  1. customThe crude product was purified

Sources & evidence

ORD record
ord-92d3fcba02ee4eb1961fc03acf64d022
Source dataset
uspto-grants-1998_12
Patent number
US05852014

Reaction notes

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