3-(3-(Piperidin-1-ylmethyl)phenoxy)propan-1-amine → HCID 20150471, compound

HRID 568358Notes

Reaction equation

HRID 568358 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.[Br:19][C:20]1[CH:25]=[CH:24][C:23]([S:26]([N:29]=[CH:30]OCC)(=[O:28])=[O:27])=[CH:22][CH:21]=1>C(O)C>[Br:19][C:20]1[CH:21]=[CH:22][C:23]([S:26]([NH:29][CH:30]=[N:15][CH2:14][CH2:13][CH2:12][O:11][C:10]2[CH:16]=[CH:17][CH:18]=[C:8]([CH2:7][N:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)[CH:9]=2)(=[O:28])=[O:27])=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 102205613-(3-(Piperidin-1-ylmethyl)phenoxy)propan-1-amineHCID 54569672Ethyl N-[(p-bromophenyl)sulfonyl]formimidate

Product 1

HCID 20150471HCID 20150471, compoundYield 67.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of 6.2 g of 3-[3-(1-piperidinylmethyl) phenoxy]-1-propanamine (prepared according to British Pat. No. 2,023,133) in 20 ml of absolute ethanol, 7.3 g of ethyl N-p-bromobenzenesulphonyl-formimidate dissolved in 20 ml of absolute ethanol are dropwise added at room temperature. The mixture is kept under stirring for 1 hour and the ethanol is removed by distillation under reduced pressure. The resulting residue is purified by dissolving in 60 ml of ethyl acetate and 25 ml of water, then acidulated with 3N hydrochloric acid up to pH2. The organic phase is case aside and the aqueous phase is basified in the presence of 20 ml of sodium acetate with 1N sodium hydroxide up to pH8. The organic phase is washed with water, dried over magnesium sulphate and evaporated till dryness. The resulting residue is chromatographied by 60 silicagel column with chloroform-methanol (8:2) as eluent. 8.3 g of N-p-bromobenzene-sulphonyl-N'-[3-[3-(1-piperidinylmethyl)phenoxy]propyl] formamidine are obtained.

Workup

  1. additionare dropwise added at room temperature
  2. customthe ethanol is removed by distillation under reduced pressure
  3. customThe resulting residue is purified
  4. dissolutionby dissolving in 60 ml of ethyl acetate
  5. washThe organic phase is washed with water
  6. dry with materialdried over magnesium sulphate
  7. customevaporated till dryness

Sources & evidence

ORD record
ord-89655a504b444b919db9a7cd20b21f57
Source dataset
uspto-grants-1988_03
Patent number
US04728655

Reaction notes

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