Tetrafluoro-m-phenylenediamine dihydrochloride → Quinacainol

HRID 65218Notes

Reaction equation

HRID 65218 reaction equation
[C:1]1([NH2:12])[C:6]([F:7])=[C:5]([F:8])[C:4]([F:9])=[C:3]([NH2:10])[C:2]=1[F:11].[ClH:13].Cl.[CH3:15][C:16]([C:19]1[CH:28]=[C:27]([C:29](=[O:38])[CH2:30][CH2:31][CH:32]2[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]2)[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:20]=1)([CH3:18])[CH3:17].C[O-].[Na+].[BH4-].[Na+]>CO>[CH3:18][C:16]([C:19]1[CH:28]=[C:27]([CH:29]([OH:38])[CH2:30][CH2:31][CH:32]2[CH2:33][CH2:34][NH:35][CH2:36][CH2:37]2)[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:20]=1)([CH3:15])[CH3:17].[C:1]1([NH2:12])[C:6]([F:7])=[C:5]([F:8])[C:4]([F:9])=[C:3]([NH2:10])[C:2]=1[F:11].[ClH:13].[ClH:13]

Participants

7

Reactant 4

HCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 4311764Sodium borohydrideHCID 10942334Sodium MethoxideHCID 155816721-[2-(1,1-Dimethyl-ethyl)-4-quinolyl]-3-(4-piperidyl)-1-propanone

Product 2

HCID 55464QuinacainolHCID 149026Tetrafluoro-m-phenylenediamine dihydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The operation was as in Example 5, starting from 14 g of the dihydrochloride of 1-[2-(1,1-dimethyl-ethyl)-4-quinolyl]-3-(4-piperidyl)-1-propanone, 4.15 g of sodium methylate and 1.8 g of sodium borohydride in 150 ml of methanol. 4.1 g were finally obtained of 1-[2-(1,1-dimethyl-ethyl)-4-quinolyl]-3-(4-piperidyl)-1-propanol (racemic), in the form of the dihydrochloride melting at 219° C.

Sources & evidence

ORD record
ord-d293db95ad074643b3f0c80070633f3e
Source dataset
uspto-grants-1986_09
Patent number
US04613607

Reaction notes

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