Sodium cyanoborohydride → 4-{[2-(1,4-Benzodioxan-2-yl)-2-hydroxyethyl]amino}piperidine

HRID 615379Notes

Reaction equation

HRID 615379 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3][CH:2]1[CH:11]([OH:14])[CH2:12][NH2:13].Cl.[NH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][C:17]1=O.C([BH3-])#N.[Na+]>C(O)C>[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3][CH:2]1[CH:11]([OH:14])[CH2:12][NH:13][CH:19]1[CH2:20][CH2:21][NH:16][CH2:17][CH2:18]1

Participants

5

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 13121298HCID 13121298, compoundHCID 20088740Piperidin-2-one--hydrogen chloride (1/1)

Product 1

HCID 204277684-{[2-(1,4-Benzodioxan-2-yl)-2-hydroxyethyl]amino}piperidine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Fifty g of [2-(1,4-benzodioxan-2-yl)-2-hydroxyethyl]amine and 85 g of piperidone HCl (ALDRICH) are dissolved in 1000 ml of ethanol. Sodium cyanoborohydride (75 g) is added, and after stirring at ambient conditions overnight (about 16 hr) the mixture is cooled and evaporated. The product is recovered by extraction with methylene chloride to yield 4-{[2-(1,4-benzodioxan-2-yl)-2-hydroxyethyl]amino}piperidine. This material is of sufficient purity to use in this invention.

Workup

  1. temperatureis cooled
  2. customevaporated
  3. customThe product is recovered by extraction with methylene chloride

Sources & evidence

ORD record
ord-dd716794465647778e632ca76c0d1fa6
Source dataset
uspto-grants-1985_02
Patent number
US04499100

Reaction notes

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