1-Bromopropane → 2-(1-Benzyl-4-propyl-4-piperidyloxy)-ethanol

HRID 329033Notes

Reaction equation

HRID 329033 reaction equation
[CH2:1](Br)[CH2:2][CH3:3].[Mg].[CH2:6]([N:13]1[CH2:22][CH2:21][C:16]2([O:20][CH2:19][CH2:18][O:17]2)[CH2:15][CH2:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>CCOCC.C1C=CC=CC=1>[CH2:6]([N:13]1[CH2:14][CH2:15][C:16]([CH2:1][CH2:2][CH3:3])([O:20][CH2:19][CH2:18][OH:17])[CH2:21][CH2:22]1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 3

HCID 78401-BromopropaneHCID 7264498-Benzyl-1,4-dioxa-8-azaspiro[4.5]decaneHCID 5462224Magnesium

Product 1

HCID 214409222-(1-Benzyl-4-propyl-4-piperidyloxy)-ethanolYield 50.5%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 108 g of propyl bromide in 250 ml of ether was added dropwise to a refluxing mixture of 19.2 g of magnesium in 100 ml of ether and then a solution of 46.6 g of 8-benzyl-1,4-dioxa-8-aza-spiro [4,5] decane in 500 ml of benzene was added in increments. The ether was evaporated off and then cooled and hydrolyzed with a saturated aqueous ammonium chloride solution. The benzene phase was decanted and the aqueous phase was extracted with ether. The ether phase was washed with water until neutral, dried over sodium sulfate and the solvents removed under reduced pressure. The residue (B.p. = 129° C at 0.1mm/Hg) was rectified to obtain 28 g of 2-(1-benzyl-4-propyl-4-piperidyloxy)-ethanol as a yellowish oil. The product was dissolved in 250 ml of ether and 13 ml of a 5N hydrogen chloride solution in ether were added thereto. The product was vacuum filtered and crystallized from isopropanol and dried in vacuo to obtain 12.9 g of 2-(1-benzyl-4-propyl-4-piperidyloxy)-ethanol hydrochloride in the form of colorless crystals melting at 196° C.

Workup

  1. customThe ether was evaporated off
  2. temperaturecooled
  3. customThe benzene phase was decanted
  4. extractionthe aqueous phase was extracted with ether
  5. washThe ether phase was washed with water until neutral,
  6. dry with materialdried over sodium sulfate
  7. customthe solvents removed under reduced pressure

Sources & evidence

ORD record
ord-e0d5e3a5af46442eb3e9f8201b74c469
Source dataset
uspto-grants-1977_04
Patent number
US04018922

Reaction notes

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