Oxalic Acid → 2-Nitro-N-[3-[3-(1-piperidinylmethyl)phenoxy]propyl]-1-(methylthio)etheneamine oxalate

HRID 444510Notes

Reaction equation

HRID 444510 reaction equation
[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:16]=[CH:17][CH:18]=2)[O:11][CH2:12][CH2:13][CH2:14][NH2:15])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:19][S:20][C:21](SC)=[CH:22][N+:23]([O-:25])=[O:24].[C:28]([OH:33])(=[O:32])[C:29]([OH:31])=[O:30]>O1CCCC1>[C:28]([OH:33])(=[O:32])[C:29]([OH:31])=[O:30].[N+:23]([CH:22]=[C:21]([S:20][CH3:19])[NH:15][CH2:14][CH2:13][CH2:12][O:11][C:10]1[CH:16]=[CH:17][CH:18]=[C:8]([CH2:7][N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[CH:9]=1)([O-:25])=[O:24]

Participants

5

Reactant 3

HCID 971Oxalic AcidHCID 836231,1-Bis(methylthio)-2-nitroethyleneHCID 102205613-(3-(Piperidin-1-ylmethyl)phenoxy)propan-1-amine

Product 1

HCID 705472272-Nitro-N-[3-[3-(1-piperidinylmethyl)phenoxy]propyl]-1-(methylthio)etheneamine oxalate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 3-[3-[(1-piperidinyl)methyl]phenoxy]propanamine (4.97 g.) and 1,1-bis-(methylthio)-2-nitroethene (6.61 g.) in tetrahydrofuran (100 ml.) was heated under reflux for 19 hours. A solution of oxalic acid (6.25%) in tetrahydrofuran (4 ml.) was added, the suspension filtered and to the filtrate was added a solution of oxalic acid (6.25%) in tetrahydrofuran (36 ml.). The solid which separated on trituration was filtered, washed with tetrahydrofuran and dried to give the title compound (7.36 g.), m.p. 71°-75°.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 19 hours
  3. filtrationthe suspension filtered and to the filtrate
  4. additionwas added a solution of oxalic acid (6.25%) in tetrahydrofuran (36 ml.)
  5. customThe solid which separated on trituration
  6. filtrationwas filtered
  7. washwashed with tetrahydrofuran
  8. customdried

Sources & evidence

ORD record
ord-f4dfae1357e942eb816f847172de3214
Source dataset
uspto-grants-1981_04
Patent number
US04264614

Reaction notes

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