Triethylamine → HCID 14570090, compound

HRID 2073296Notes

Reaction equation

HRID 2073296 reaction equation
[C:1]1([C:7]2[CH:8]=[C:9]([CH:13]=[CH:14][C:15]=2[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:10](O)=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.C(N(CC)CC)C.[N:46]1[CH:51]=[CH:50][CH:49]=[C:48]([CH2:52][CH2:53][CH2:54][CH2:55][NH2:56])[CH:47]=1>CN(C=O)C>[C:1]1([C:7]2[CH:8]=[C:9]([CH:13]=[CH:14][C:15]=2[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:10]([NH:56][CH2:55][CH2:54][CH2:53][CH2:52][C:48]2[CH:47]=[N:46][CH:51]=[CH:50][CH:49]=2)=[O:11])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 72927Pyridine, 3-(4-aminobutyl)-HCID 199401P,P-Diphenylphosphinic azideHCID 14570138HCID 14570138, compound

Product 1

HCID 14570090HCID 14570090, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To an ice-cooled solution of 0.508 g 1.85 mmol) of 3,4-diphenylbenzoic acid in 10 mL of anhydrous DMF was added 0.44 mL of diphenylphosphoryl azide with stirring. Triethylamine (0.28 mL) was then added and stirring at 3° C. 0 was continued for 1 hour. 3-pyridinebutanamine (0.309 g) was added and stirring was continue for 30 minutes at 3° C. and for 17 hours at room temperature. The solvent was removed under the oil pump vacuum and ethyl acetate was added to the residue. The solution was washed with aqueous 5% sodium bicarbonate. dried (MgSO4) and concentrated in vacuo. The residual oil was chromatographed on 50 g of silica gel, eluting with methylene chloride-methanol-conc.ammonium hydroxide (95:5:0.05). The pure fractions were combined and lyophilized from benzene to yield a 0.708 g of 3,4-Diphenyl-N-[4-(3-pyridinyl)butyl]benzamide 0.25 molar hydrate as a colorless foam.

Workup

  1. stirringstirring at 3° C
  2. stirringstirring
  3. waitwas continue for 30 minutes at 3° C. and for 17 hours at room temperature
  4. customThe solvent was removed under the oil pump vacuum and ethyl acetate
  5. additionwas added to the residue
  6. washThe solution was washed with aqueous 5% sodium bicarbonate
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo
  9. customThe residual oil was chromatographed on 50 g of silica gel
  10. washeluting with methylene chloride-methanol-conc

Sources & evidence

ORD record
ord-6d39ea72791a4098bb34f6511fc46cdd
Source dataset
uspto-grants-1990_04
Patent number
US04916145

Reaction notes

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