Phenacyl bromide → HCID 20559862, compound

HRID 1659210Notes

Reaction equation

HRID 1659210 reaction equation
[CH2:1]([N:6]([CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[C:7]1[CH2:16][CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=1)[CH2:2][CH2:3][CH2:4][CH3:5].[CH2:22]([Br:31])[C:23]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:24]>>[Br-:31].[O:24]=[C:23]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:22][CH:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:15][CH2:16][C:7]1=[N+:6]([CH2:1][CH2:2][CH2:3][CH3:4])[CH2:17][CH2:18][CH2:19][CH3:20].[BrH:31].[CH2:22]([C:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:15][CH2:16][C:7]=1[N:6]([CH2:1][CH2:2][CH2:3][CH3:4])[CH2:17][CH2:18][CH2:19][CH3:20])[C:23]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:24].[Br-:31].[O:24]=[C:23]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:22][CH:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:15][CH2:16][C:7]1=[N+:6]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21].[BrH:31].[CH2:22]([C:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:15][CH2:16][C:7]=1[N:6]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[C:23]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:24]

Participants

6

Reactant 2

HCID 6259Phenacyl bromideHCID 20559878HCID 20559878, compound

Product 4

HCID 20559862HCID 20559862, compoundHCID 20559864HCID 20559864, compoundHCID 20559872HCID 20559872, compoundHCID 20559876HCID 20559876, compound

Procedure

By following the method of Example 1a the treatment of ⟦2-di-n-butylamino-3,4-dihydro-naphthalene,2-diamylamino-3,4-dihydronaphthalene, ⟧2-di-n-butylamino-3,4-dihydronaphthalene, 2-diamylamino-3,4-dihydronaphthalene, and 2-(1-piperidino)-3,4-dihydronaphthalene with phenacylbromide produces tautomeric N-[3,4-dihydro-1-(2-oxo-2-phenylethyl)-2(1H)-naphthalenylidene]-N-butyl-butanaminium bromide in equilibrium with 1-phenacyl-2-di-n-butylamino-3,4-dihydronaphthalene hydrobromide, tautomeric N-[3,4-dihydro-1-(2-oxo-2-phenylethyl)-2(1H)-naphthalenylidene]-N-pentyl-pentanaminium bromide in equilibrium with 1-phenacyl-2-diamylamino-3,4-dihydronaphthalene hydrobromide, and tautomeric 1-[3,4-dihydro-1-(2-oxo-2-phenylethyl-2(1H)-naphthalenylidene]piperidinium bromide in equilibrium with 1-phenacyl-2-(1-piperidino)-3,4-dihydronaphthalene hydrobromide, respectively.

Sources & evidence

ORD record
ord-81c38011be974108904d90ec49152a60
Source dataset
uspto-grants-1981_12
Patent number
USRE030809

Reaction notes

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