Diethyl Ether → 2-[[[3-(1-Piperidinylmethyl)phenyl]methyl]thio]ethanamine

HRID 35039Notes

Reaction equation

HRID 35039 reaction equation
[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH2:14]O)[CH:11]=[CH:12][CH:13]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.[NH2:17][CH2:18][CH2:19][SH:20].CCOCC.C(=O)([O-])[O-].[Na+].[Na+]>Cl>[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH2:14][S:20][CH2:19][CH2:18][NH2:17])[CH:11]=[CH:12][CH:13]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 9082Cysteamine HydrochlorideHCID 10340Sodium CarbonateHCID 7164645(3-((Piperidin-1-yl)methyl)phenyl)methanol

Product 1

HCID 212975442-[[[3-(1-Piperidinylmethyl)phenyl]methyl]thio]ethanamineYield 68.4%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of 3-(1-piperidinylmethyl)benzenemethanol (10.8 g) and cysteamine hydrochloride (6.48 g) in concentrated hydrochloric acid (25 ml) was heated at 100° for 3 h. The cooled mixture was added to ether (500 ml) and treated with an excess of sodium carbonate. The organic solution was filtered and distilled to give the title compound as an oil (9.51 g) b.p. 175° (6×10-2 mm). TLC silica; ethyl acetate:water:isopropanol:0.88 ammonia 25:8:15:2; Rf 0.7.

Workup

  1. temperaturewas heated at 100° for 3 h
  2. filtrationThe organic solution was filtered
  3. distillationdistilled

Sources & evidence

ORD record
ord-3b10d310c9224effbd340e6cb1c8df52
Source dataset
uspto-grants-1988_08
Patent number
US04764612

Reaction notes

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