Carbon Tetrachloride → 1-(2-Chloroethyl)-1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indole

HRID 901058Notes

Reaction equation

HRID 901058 reaction equation
[CH2:1]([C:3]1([CH2:18][CH2:19]O)[C:8]2[NH:9][C:10]3[C:15]([C:7]=2[CH2:6][CH2:5][O:4]1)=[CH:14][CH:13]=[CH:12][C:11]=3[CH2:16][CH3:17])[CH3:2].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(Cl)(Cl)(Cl)[Cl:41]>O>[Cl:41][CH2:19][CH2:18][C:3]1([CH2:1][CH3:2])[C:8]2[NH:9][C:10]3[C:15]([C:7]=2[CH2:6][CH2:5][O:4]1)=[CH:14][CH:13]=[CH:12][C:11]=3[CH2:16][CH3:17]

Participants

5

Reactant 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 108910512-(1,8-Diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)-ethanol

Product 1

HCID 219075721-(2-Chloroethyl)-1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indoleYield 51%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of compound 1 (136 mg, 0.5 mmol), PPh3 (262 mg, 1.0 mmol, 2.0 eq), and CCl4 (2.5 mL) was refluxed overnight. The resulting mixture was then diluted with water and extracted three times with CH2Cl2. The organic phases were combined, dried with Na2SO4, concentrated, and purified by column chromatography using 5:95:EtOAc:Hexane to give a white solid (74 mg, 51%): mp 106-107° C. (dec). 1HNMR (CDCl3, δ TMS): 0.93 (t, 3H), 1.37 (t, 3H), 1.91 (m, 2H), 2.34 (m, 2H), 2.76 (m, 2H), 2.87 (q, 2H), 3.46 (dm, 2H), 3.99 (m, 2H), 7.04-7.38 (m, 3H, Ar—H), 7.55 (br, 1H, NH). MS−: m/z 326 (MCl−), 290 ([M−H]−). Anal. (C17H22NOCl): C, H, N.

Workup

  1. extractionextracted three times with CH2Cl2
  2. dry with materialdried with Na2SO4
  3. concentrationconcentrated
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-93f84b78654546f988253242b342eb3d
Source dataset
uspto-grants-2008_04
Patent number
US07361680B2

Reaction notes

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