Triethylamine → HCID 15257493, compound

HRID 2107655Notes

Reaction equation

HRID 2107655 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5](/[CH:18]=[CH:19]/[CH:20]=[CH:21]/[C:22]([OH:24])=O)[CH:6]=[C:7]([O:16][CH3:17])[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.[NH2:47][CH2:48][CH2:49][N:50]1[CH2:55][CH2:54][CH:53]([C:56]2[C:64]3[C:59](=[CH:60][CH:61]=[CH:62][CH:63]=3)[NH:58][CH:57]=2)[CH2:52][CH2:51]1>CN(C)C=O>[CH3:17][O:16][C:7]1[CH:6]=[C:5](/[CH:18]=[CH:19]/[CH:20]=[CH:21]/[C:22]([NH:47][CH2:48][CH2:49][N:50]2[CH2:51][CH2:52][CH:53]([C:56]3[C:64]4[C:59](=[CH:60][CH:61]=[CH:62][CH:63]=4)[NH:58][CH:57]=3)[CH2:54][CH2:55]2)=[O:24])[CH:4]=[C:3]([O:2][CH3:1])[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 15257491HCID 15257491, compoundHCID 15257492HCID 15257492, compound

Product 1

HCID 15257493HCID 15257493, compoundYield 87.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a stirred mixture of 5-[3,5-dimethoxy-4-{(2-methoxyethoxy)methoxy}phenyl]-(2E,4E)-2,4-pentadienoic acid (1.35 g) and triethylamine (1.17 ml) in dry N,N-dimethylformamide (8 ml) was added slowly diphenyl phosphinic chloride (0.97 g) at -10° to -15° C. under an inert atmosphere. After being stirred for 1 hour, a solution of 1-(2-aminoethyl)-4-(3-indolyl)piperidine (0.97 g) in dry N,N-dimethylformamide (8 ml) was added slowly to the reaction mixture at the same temperature. After being stirred for 40 minutes at the same temperature, the reaction mixture was poured into ice-water (160 ml) and extracted with ethyl acetate. The extract was washed with a saturated sodium chloride solution and dried over magnesium sulfate. The solvent was evaporated to give syrup of 1-[2-[5-[3,5-dimethoxy-4-{(2-methoxyethoxy)methoxy}phenyl]-(2E,4E)-2,4-pentadienoylamino]ethyl]-4-(3-indolyl)piperidine (1.97 g).

Workup

  1. stirringAfter being stirred for 40 minutes at the same temperature
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with a saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-815efe50c3c748f880b98e865bff570c
Source dataset
uspto-grants-1990_06
Patent number
US04935432

Reaction notes

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