Diisopropylethylamine → HCID 19024728, compound

HRID 249180Notes

Reaction equation

HRID 249180 reaction equation
[CH2:1]([NH:8][C:9]1[CH:10]=[C:11]([CH:36]=[CH:37][CH:38]=1)[C:12]([C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]([CH2:23][CH2:24][CH2:25][C:26]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[O:27])[CH:15]=1)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.Br[CH:49]([C:52]1[CH:57]=[CH:56][C:55]([CH2:58][CH:59]([CH3:61])[CH3:60])=[CH:54][CH:53]=1)[CH2:50][CH3:51]>ClCCl>[CH2:1]([N:8]([C:9]1[CH:10]=[C:11]([CH:36]=[CH:37][CH:38]=1)[CH2:12][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]([CH2:23][CH2:24][CH2:25][C:26]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[O:27])[CH:15]=1)[CH:49]([C:52]1[CH:53]=[CH:54][C:55]([CH2:58][CH:59]([CH3:60])[CH3:61])=[CH:56][CH:57]=1)[CH2:50][CH3:51])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 10956141Benzene, 1-(1-bromopropyl)-4-(2-methylpropyl)-HCID 19024820Benzyl 4-[3-(3-benzylaminobenzoyl)indol-1-yl]butyrate

Product 1

HCID 19024728HCID 19024728, compoundYield 25.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of benzyl 4-[3-(3-benzylaminobenzoyl)indol-1-yl]butyrate (88 mg) and diisopropylethylamine (45 mg) in dichloromethane (3 ml) was added a solution of 1-bromo-1-(4-isobutylphenyl)propane (90 mg) in dichloromethane (1 ml). The mixture was stirred at room temperature for 24 hours and evaporated. The residue was dissolved in ethyl acetate. The solution was washed with water, dried over magnesium sulfate and evaporated. The residue was chromatographed on silica gel (5 g) eluting with a mixture of n-hexane and ethyl acetate (4:1) to give benzyl 4-[3-[3-[N-benzyl-N-[1-(4-isobutylphenyl)propyl]amino]benzyl]indol-1-yl]butyrate (30 mg) as an oil.

Workup

  1. customevaporated
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washThe solution was washed with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe residue was chromatographed on silica gel (5 g)
  7. washeluting with a mixture of n-hexane and ethyl acetate (4:1)

Sources & evidence

ORD record
ord-fe81d29440864b2a9bef95d9541633be
Source dataset
uspto-grants-1993_05
Patent number
US05212320

Reaction notes

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