Triphenylphosphine → HCID 18933652, compound

HRID 1598301Notes

Reaction equation

HRID 1598301 reaction equation
[CH2:1]([N:8]([CH3:12])[CH2:9][CH2:10][OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[Cl:44][C:45]1[C:46]([CH2:52][N:53]([CH3:55])[CH3:54])=[C:47](O)[CH:48]=[CH:49][CH:50]=1>C1COCC1>[ClH:44].[ClH:44].[CH2:1]([N:8]([CH2:9][CH2:10][O:11][C:47]1[CH:48]=[CH:49][CH:50]=[C:45]([Cl:44])[C:46]=1[CH2:52][N:53]([CH3:54])[CH3:55])[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 66876N-Benzyl-N-methylethanolamineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 18933655HCID 18933655, compound

Product 1

HCID 18933652HCID 18933652, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-Benzyl-N-methylethanolamine (5.25 ml), triphenylphosphine (8.48 g) and diethyl azodicarboxylate (5.09 ml) were added to a solution of 3-chloro-2-(dimethylaminomethyl)phenol (6.0 g) in dry THF (200 ml) at ambient temperature with stirring under nitrogen. The mixture was stirred at ambient temperature for 24 hours and then evaporated to dryness under reduced pressure at 30° C. The residue was dissolved in 2M hydrochloric acid, washed with ethyl acetate, and then basified with concentrated sodium hydroxide solution. The mixture was extracted with dichloromethane to give an oil which was distilled under vacuum in a Kugelrohr. The higher boiling fraction which boiled at 140° C. at 0.01 mbar was dissolved in ether and treated with ethereal hydrogen chloride. The mixture was filtered and the solid collected was recrystallised from propan-2-ol to give 2-[2-(N-benzyl-N-methylamino)ethoxy]-6-chloro-N,N-dimethylbenzylamine dihydrochloride, m.p. 238°-239° C.

Workup

  1. stirringThe mixture was stirred at ambient temperature for 24 hours
  2. customevaporated to dryness under reduced pressure at 30° C
  3. dissolutionThe residue was dissolved in 2M hydrochloric acid
  4. washwashed with ethyl acetate
  5. extractionThe mixture was extracted with dichloromethane
  6. customto give an oil which
  7. distillationwas distilled under vacuum in a Kugelrohr
  8. dissolutionThe higher boiling fraction which boiled at 140° C. at 0.01 mbar was dissolved in ether
  9. additiontreated with ethereal hydrogen chloride
  10. filtrationThe mixture was filtered
  11. customthe solid collected
  12. customwas recrystallised from propan-2-ol

Sources & evidence

ORD record
ord-3b5e4e32c60b440e9b4829c81c0719a8
Source dataset
uspto-grants-1998_04
Patent number
US05736568

Reaction notes

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