p-Toluenesulfonic acid → HCID 22147750, compound

HRID 1824298Notes

Reaction equation

HRID 1824298 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][C:2]1=O.[NH:12]1[CH2:17][CH:16]([C:18]([NH2:20])=[O:19])[O:15][CH2:14][CH2:13]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O>[C:1]1(=[O:15])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[NH:12]1[CH2:17][CH:16]([C:18]([NH2:20])=[O:19])[O:15][CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 22147728HCID 22147728, compound2×

Product 1

HCID 22147750HCID 22147750, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-Tetralone-6-morpholinamide, ethylene ketal (323 mg, 1.06 mmol) and catalytic p-toluenesulfonic acid were stirred in acetone (50 mL) at ambient temperature for 48 hours. TLC indicated a mixture of 2-tetralone-6-morpholinamide, ethylene ketal and desired product, so the solution was heated to reflux for 16 hours. The volatiles were removed in vacuo and the residue applied to a silica flash chromatography column and eluted with 50–100% EtOAc in hexanes to yield 27 mg (10%) of 2-tetralone-6-morpholinamide a slowly crystallizing solid, pure by NMR, TLC. MS.

Sources & evidence

ORD record
ord-a311ba663a75400ebc9b91c0ea80185a
Source dataset
uspto-grants-2006_05
Patent number
US07041684B2

Reaction notes

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