Triethylamine → HCID 18973992, compound

HRID 2395038Notes

Reaction equation

HRID 2395038 reaction equation
C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[N:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH2:24][C:25]([OH:27])=O.C(N(CC)CC)C.Cl.[CH2:36]([O:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][C:45]=1[CH2:50][CH2:51][CH2:52][C:53]1[CH:58]=[CH:57][C:56]([NH2:59])=[CH:55][CH:54]=1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>CN(C)C=O>[CH2:36]([O:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][C:45]=1[CH2:50][CH2:51][CH2:52][C:53]1[CH:58]=[CH:57][C:56]([NH:59][C:25]([CH2:24][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][N:18]=2)=[O:27])=[CH:55][CH:54]=1)[C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1

Participants

6

Reactant 4

HCID 8471Triethylamine2×HCID 853182-Pyridineacetic acidHCID 199401P,P-Diphenylphosphinic azideHCID 18973995HCID 18973995, compound

Product 1

HCID 18973992HCID 18973992, compoundYield 68.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

Diphenylphosphoryl azide (0.46 ml) was added dropwise to a stirred suspension of 2-pyridylacetic acid (0.367 g) and triethylamine (0.3 ml) in N,N-dimethylformamide (10 ml) maintained at 0° C. A suspension of 4-[3-(2-benzyloxyphenyl)propyl]benzeneamine hydrochloride (0.75 g) in N,N-dimethylformamide (10 ml) containing triethylamine (0.9 ml) was added rapidly to the reaction mixture. Stirring was continued at ambient temperature for 16 hours and the reaction mixture was concentrated to small volume. The residue was partitioned between water and diethyl ether. The diethyl ether extract was washed once each with saturated aqueous sodium bicarbonate (20 ml) and brine (20 ml) and dried. The gum obtained on removal of the solvent was subjected to chromatography on silica (Merck 9385) eluted with a mixture of ethyl acetate and hexane (1:1 v/v). The gum obtained was triturated with ether at 0° C. to give 4-[3-(2-benzyloxy-phenyl)propyl]-N-(2-pyridylmethylcarbonyl)benzeneamine (m.p. 61°-2° C.; yield 0.63 g 68%).

Workup

  1. additionwas added rapidly to the reaction mixture
  2. concentrationthe reaction mixture was concentrated to small volume
  3. customThe residue was partitioned between water and diethyl ether
  4. extractionThe diethyl ether extract
  5. washwas washed once each with saturated aqueous sodium bicarbonate (20 ml) and brine (20 ml)
  6. customdried
  7. customThe gum obtained on removal of the solvent
  8. washeluted with a mixture of ethyl acetate and hexane (1:1 v/v)
  9. customThe gum obtained
  10. customwas triturated with ether at 0° C.

Sources & evidence

ORD record
ord-3874339bbc4f49a6a1d1aa7ec06d6f9a
Source dataset
uspto-grants-1998_09
Patent number
US05811459

Reaction notes

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