Methanol → 1-(2-Hydroxy-3-n-hexadecyloxypropyl)-piperazine

HRID 1106273Notes

Reaction equation

HRID 1106273 reaction equation
Cl.C([N:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH:16]([OH:35])[CH2:17][O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH2:11][CH2:10]1)C1C=CC=CC=1.CO.O1CCCC1.[H][H]>C1(C)C=CC=CC=1.[Pd]>[OH:35][CH:16]([CH2:17][O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH2:15][N:12]1[CH2:13][CH2:14][NH:9][CH2:10][CH2:11]1

Participants

7

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 205538111-Benzyl-4-(2-hydroxy-3-n-hexadecyloxypropyl)-piperazine hydrochlorideHCID 178418361HCID 178418361, compound

Product 1

HCID 130377901-(2-Hydroxy-3-n-hexadecyloxypropyl)-piperazine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1140TolueneSolvent

Procedure

1-Benzyl-4-(2-hydroxy-3-n-hexadecyloxypropyl)-piperazine hydrochloride (8 g, 0.0146 mol) was dissolved in toluene (100 ml), methanol (100 ml) and tetrahydrofuran (700 ml) and divided into three 300 ml portions. Each portion was hydrogenated overnight at room temperature on a Parr shaker using a 10% palladium on carbon catalyst (2 g) and 50 p.s.i.g. hydrogen. The catalyst was filtered off and the filtrate evaporated under reduced pressure to a solid, which was triturated under acetone and filtered to give a total yield of product of 2.9 g (43%), mp 230° C. (dec).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate evaporated under reduced pressure to a solid, which
  3. customwas triturated under acetone
  4. filtrationfiltered
  5. customto give a total yield of product of 2.9 g (43%), mp 230° C. (dec)

Sources & evidence

ORD record
ord-a446b825906a40cba68307bddfc59561
Source dataset
uspto-grants-1982_01
Patent number
US04312877

Reaction notes

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