Ammonium Chloride → HCID 20207293, compound

HRID 542786Notes

Reaction equation

HRID 542786 reaction equation
[N:1]1([CH2:7][C:8]2[CH:9]=[C:10](Br)[CH:11]=[CH:12][CH:13]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Mg].[CH2:16]([NH:23][CH2:24][CH:25]1[CH2:27][O:26]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[Cl-].[NH4+]>O1CCCC1>[CH2:16]([N:23]([CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[CH2:24][CH:25]([OH:26])[CH2:27][C:10]1[CH:11]=[CH:12][CH:13]=[C:8]([CH2:7][N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[CH:9]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 38470661-(3-Bromobenzyl)piperidineHCID 5462224MagnesiumHCID 1063084680236-09-5

Product 1

HCID 20207293HCID 20207293, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
60 °C

Procedure

10.2 g (0.04 mol) of 3-(1-piperidylmethyl)-bromobenzene in 20 ml of tetrahydrofuran are added dropwise to 0.97 g (0.04 mol) of magnesium filings in 5 ml of tetrahydrofuran at a reaction temperature of 60° C. This operation is followed by 30 minutes' stirring at 60° C., and the solution is then cooled to 10° C. 10.2 g (0.04 mol) of 2-benzylaminomethyl-oxirane in 20 ml of tetrahydrofurane are slowly added dropwise and the solution obtained is stirred at room temperature for 2 hours. After the addition of 20 ml of ice water and 4.5 g of ammonium chloride, the aqueous phase is separated and extracted with 25 ml of methylene chloride. The combined organic phases are dehydrated with sodium sulphate and concentrated by evaporation to yield a yellow resin which is chromatographed with methylene chloride/methanol (9:1) against silica gel. After concentration by evaporation, the second fraction yields the title compound as a pale yellow oil.

Workup

  1. temperaturethe solution is then cooled to 10° C
  2. customthe solution obtained
  3. stirringis stirred at room temperature for 2 hours
  4. customthe aqueous phase is separated
  5. extractionextracted with 25 ml of methylene chloride
  6. concentrationconcentrated by evaporation
  7. customto yield a yellow resin which
  8. customis chromatographed with methylene chloride/methanol (9:1) against silica gel
  9. concentrationAfter concentration
  10. customby evaporation

Sources & evidence

ORD record
ord-749847d6ca77459bb1360b14d8f5eee3
Source dataset
uspto-grants-1987_04
Patent number
US04659721

Reaction notes

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