Epichlorohydrin → HCID 68124417, compound

HRID 597740Notes

Reaction equation

HRID 597740 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][C:3]2([CH2:11][CH:10]3[CH2:12][CH:7]2[CH2:8][CH2:9]3)[CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[CH2:19]([CH:21]1[O:23][CH2:22]1)[Cl:20]>C(O)C>[ClH:20].[Cl:20][CH2:19][CH:21]([OH:23])[CH2:22][N:1]1[CH2:6][CH2:5][CH2:4][C:3]2([CH2:11][CH:10]3[CH2:12][CH:7]2[CH2:8][CH2:9]3)[CH2:2]1

Participants

5

Reactant 3

HCID 7835EpichlorohydrinHCID 11430Potassium CarbonateHCID 21446161HCID 21446161, compound

Product 1

HCID 68124417HCID 68124417, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

24.9 g (0.15 mole) of (1RS,2RS,4SR)-spiro[norbornane-2,3'-piperidine] and 25 g of potassium carbonate are suspended in 100 ml of ethanol; an addition of 15.0 g (0.11 mole) of epichlorohydrin (1-chloro-2,3-epoxypropane) is subsequently made, whereupon the mixture heats up to 40°. It is stirred for 16 hours at room temperature and then concentrated in vacuo (ca. 12 Torr). The residue is suspended in 150 ml of water, and extracted three times with 50 ml of chloroform each time. The chloroform extracts are washed separately three times with 50 ml of water each time, dried over sodium sulphate and concentrated by evaporation. The residue is dissolved in 200 ml of 2N hydrochloric acid; this solution is extracted once with 50 ml of chloroform and concentrated in vacuo (ca. 12 Torr). The obtained reddish crystals are recrystallised from acetone/ether to obtain α-(chloromethyl)-(1RS,2RS,4SR)-spiro[norbornane-2,3'-piperidine]-1' -ethanol-hydrochloride, M.P. 199°-201°.

Workup

  1. customheats up to 40°
  2. concentrationconcentrated in vacuo (ca. 12 Torr)
  3. extractionextracted three times with 50 ml of chloroform each time
  4. washThe chloroform extracts are washed separately three times with 50 ml of water each time
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated by evaporation
  7. dissolutionThe residue is dissolved in 200 ml of 2N hydrochloric acid
  8. extractionthis solution is extracted once with 50 ml of chloroform
  9. concentrationconcentrated in vacuo (ca. 12 Torr)
  10. customThe obtained reddish crystals are recrystallised from acetone/ether

Sources & evidence

ORD record
ord-d0cd5badc66c4252a53be901a39c895c
Source dataset
uspto-grants-1977_03
Patent number
US04015007

Reaction notes

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