Triethylamine → HCID 15257507, compound

HRID 2107647Notes

Reaction equation

HRID 2107647 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5](/[CH:16]=[CH:17]/[C:18]([OH:20])=O)[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][O:11][CH2:12][CH2:13][O:14][CH3:15].C(N(CC)CC)C.C1(P(Cl)(C2C=CC=CC=2)=O)C=CC=CC=1.[NH2:43][CH2:44][CH2:45][N:46]1[CH2:51][CH2:50][CH:49]([C:52]2[C:60]3[C:55](=[CH:56][CH:57]=[CH:58][CH:59]=3)[NH:54][CH:53]=2)[CH2:48][CH2:47]1>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5](/[CH:16]=[CH:17]/[C:18]([NH:43][CH2:44][CH2:45][N:46]2[CH2:47][CH2:48][CH:49]([C:52]3[C:60]4[C:55](=[CH:56][CH:57]=[CH:58][CH:59]=4)[NH:54][CH:53]=3)[CH2:50][CH2:51]2)=[O:20])[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][O:11][CH2:12][CH2:13][O:14][CH3:15]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 73910Diphenylphosphinic chlorideHCID 13711151HCID 13711151, compoundHCID 15257492HCID 15257492, compound

Product 1

HCID 15257507HCID 15257507, compoundYield 89.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a stirred mixture of 3-[3-methoxy-4-{(2-methoxyethoxy)methoxy}phenyl]-(E)-propenoic acid (1.75 g) and triethylamine (1.81 ml) in dry N,N-dimethylformamide (10 ml) was added slowly diphenyl phosphinic chloride (1.47 g) at -10° to -15° C. under an inert atmosphere. After being stirred for 30 minutes, a solution of 1-(2-aminoethyl)-4-(3-indolyl)piperidine (1.5 g) in dry N,N-dimethylformamide (10 ml) was added slowly to the reaction mixture at -10° C. After being stirred for 1 hour at ambient temperature, the reaction mixture was poured into ice-water (200 ml) and extracted with chloroform (100 ml). The extract was washed with a saturated sodium chloride solution and dried over magnesium sulfate. The solvent was distilled off and the residue was subjected to column chromatography on silicagel (47 g) and eluted with a mixture of chloroform and methanol (10:1). The fractions containing the object compound were combined and concentrated under reduced pressure to give syrup of 1-[2-[3-[3-methoxy-4-{(2-methoxyethoxy)methoxy}phenyl]-(E)-propenoylamino]ethyl]-4-(3-indolyl)piperidine (2.8 g).

Workup

  1. stirringAfter being stirred for 1 hour at ambient temperature
  2. extractionextracted with chloroform (100 ml)
  3. washThe extract was washed with a saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. distillationThe solvent was distilled off
  6. washeluted with a mixture of chloroform and methanol (10:1)
  7. additionThe fractions containing the object compound
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3898bf484a8544cab7c945ac9717d032
Source dataset
uspto-grants-1990_06
Patent number
US04935432

Reaction notes

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