1-Iodopropane → HCID 22842843, compound

HRID 256570Notes

Reaction equation

HRID 256570 reaction equation
[CH3:1][C@@H:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[Br:12])[CH2:5][CH2:4][C@@H:3]1[NH:13][CH2:14][CH2:15][CH3:16].I[CH2:18][CH2:19][CH3:20].CN(C1C2C(N(C)C)=CC=CC=2C=CC=1)C>C(#N)C>[CH3:1][C@@H:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[Br:12])[CH2:5][CH2:4][C@@H:3]1[N:13]([CH2:18][CH2:19][CH3:20])[CH2:14][CH2:15][CH3:16]

Participants

5

Reactant 3

HCID 336431-IodopropaneHCID 88675Proton spongeHCID 22842845HCID 22842845, compound

Product 1

HCID 22842843HCID 22842843, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of cis-1-Methyl-2-n-propylamino-8-bromo-1,2,3,4-tetrahydronaphthalene (1.47 gm, 5.2 mMol) in acetonitrile (30 mL) were added 1-iodopropane (0.59 mL, 5.8 mMol) and proton sponge (2.2 gm, 10.4 mMol), and the mixture was stirred at 50° C. for eighteen hours. The colorless suspension was filtered and the filtrate concentrated in vacuo to give a light yellow oil. Purification by flash chromatography (20% diethyl ether in hexane+tr. NH4OH) gave the desired compound as a colorless glass (330 mg, 20%).

Workup

  1. filtrationThe colorless suspension was filtered
  2. concentrationthe filtrate concentrated in vacuo
  3. customto give a light yellow oil
  4. customPurification by flash chromatography (20% diethyl ether in hexane+tr. NH4OH)

Sources & evidence

ORD record
ord-ecb35d1176164a2fab899895ceb904cc
Source dataset
uspto-grants-1993_11
Patent number
US05258379

Reaction notes

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