Water → HCID 54096843, compound

HRID 1155203Notes

Reaction equation

HRID 1155203 reaction equation
[CH3:1][Li].[CH2:3]([CH:10]1[C:15](=[O:16])[CH2:14][CH2:13][CH2:12][N:11]1[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].O>CCOCC>[CH2:3]([CH:10]1[C:15]([OH:16])([CH3:1])[CH2:14][CH2:13][CH2:12][N:11]1[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

5

Reactant 3

HCID 962WaterHCID 53694893HCID 53694893, compoundHCID 178418348HCID 178418348, compound2×

Product 1

HCID 54096843HCID 54096843, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Methyl lithium (7 ml, 2 M solution in ether) was injected, under nitrogen, into a stirred solution of 2-n-heptyl-1-n-octylpiperidin-3-one (3.4 g) in dry ether (100 ml) at -78°. The mixture was allowed to warm gradually to room temperature. After 3 hours, thin layer chromatography indicated that some starting material remained. The solution was cooled to -78° and methyl lithium (3 ml, 2 M solution in ether) was injected. The mixture was allowed to warm gradually to room temperature and was allowed to stand for 2 days. Water (10 ml) was added dropwise and the ether phase was separated, dried over magnesium sulphate and evaporated in vacuo. The product was purified by column chromatography to give 2-n-heptyl-3-hydroxy-3-methyl-1-n-octylpiperidine as a yellow gum (1.47 g, 41% yield).

Workup

  1. temperatureThe solution was cooled to -78°
  2. temperatureto warm gradually to room temperature
  3. waitto stand for 2 days
  4. customthe ether phase was separated
  5. dry with materialdried over magnesium sulphate
  6. customevaporated in vacuo
  7. customThe product was purified by column chromatography

Sources & evidence

ORD record
ord-7be3fa90fc0d40b393d0414fc19760e7
Source dataset
uspto-grants-1981_11
Patent number
US04299970

Reaction notes

Loading…