Chloride → 4-{[2-(1,4-Benzodioxan-2-yl)-2-hydroxyethyl]amino}-[(2,6-dimethylphenyl)aminocarbonylmethyl]piperidine

HRID 615380Notes

Reaction equation

HRID 615380 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[NH:9][C:10]([CH2:12][N:13]1[CH2:18][CH2:17][C:16](=O)[CH2:15][CH2:14]1)=[O:11].[Cl-].[O:21]1[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2[O:24][CH2:23][CH:22]1[CH:31]([OH:34])[CH2:32][NH2:33].N1CCCCC1.C([BH3-])#N.[Na+]>>[O:21]1[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2[O:24][CH2:23][CH:22]1[CH:31]([OH:34])[CH2:32][NH:33][CH:16]1[CH2:17][CH2:18][N:13]([CH2:12][C:10]([NH:9][C:3]2[C:2]([CH3:1])=[CH:7][CH:6]=[CH:5][C:4]=2[CH3:8])=[O:11])[CH2:14][CH2:15]1

Participants

6

Reactant 5

HCID 312ChlorideHCID 8082PiperidineHCID 5003444Sodium cyanoborohydrideHCID 13121298HCID 13121298, compoundHCID 133933531-[(2,6-Dimethylphenyl)aminocarbonylmethyl]-4-piperidone

Product 1

HCID 133933564-{[2-(1,4-Benzodioxan-2-yl)-2-hydroxyethyl]amino}-[(2,6-dimethylphenyl)aminocarbonylmethyl]piperidine

Procedure

Substituting into the procedure of Example 1, 1-[(2,6-dimethylphenyl)aminocarbonylmethyl]-4-piperidone for the corresponding chloride and [2-(1,4-benzodioxan-2-yl)-2-hydroxyethyl]amine or amine hydrochloride, rather than the corresponding piperidine and adding 75 g of sodium cyanoborohydride, one obtains 4-{[2-(1,4-benzodioxan-2-yl)-2-hydroxyethyl]amino}-1-[(2,6-dimethylphenyl)aminocarbonylmethyl]piperidine compound.

Sources & evidence

ORD record
ord-a5ed76f27e38421e91d30b6d95782757
Source dataset
uspto-grants-1985_02
Patent number
US04499100

Reaction notes

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