1,2,3,4-Tetrahydroisoquinoline → HCID 9882311, compound

HRID 1978908Notes

Reaction equation

HRID 1978908 reaction equation
[CH:1]1[CH:5]=[C:4]([C:6]([CH2:8][CH2:9][CH2:10]Cl)=[O:7])[S:3][CH:2]=1.[CH2:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][CH2:14][NH:13]1>>[O:7]=[C:6]([C:4]1[S:3][CH:2]=[CH:1][CH:5]=1)[CH2:8][CH2:9][CH2:10][N:13]1[CH2:14][CH2:15][C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:12]1

Participants

3

Reactant 2

HCID 70461,2,3,4-TetrahydroisoquinolineHCID 1235114-Chloro-1-(2-thienyl)butan-1-one

Product 1

HCID 9882311HCID 9882311, compoundYield 58%

Procedure

Prepared in standard fashion from commercially available 4-chloro-2′-butyrothienone and 1,2,3,4-tetrahydroisoquinoline. Purified by flash chromatography, eluting with 1:1 EtOAc/hexane to provide 17A (58% yield) as a yellow oil. 1H NMR(300 MHz, CDCl3, δ): 7.72-7.70 (m, 1H), 7.60-7.58 (m, 1H), 7.15-6.98 (m, 5H), 3.62 (s, 2H), 3.01 (t, 2H, J=7 Hz), 2.87 (t, 2H, J=6 Hz), 2.72 (t, 2H, J=6 Hz), 2.59 (t, 2H, J=7 Hz), 2.10-2.00 (m, 2H). C NMR(300 MHz, CDCl3, δ): 193.10, 144.56, 134.92, 134.43, 133.34, 131.79, 128.64, 128.05, 126.59, 126.08, 125.58, 57.37, 56.10, 50.83, 37.01, 29.19, 22.14. . IR(KBr, cm−1): 1662 (s). UV(MeOH): )max 282 nm, ε260. MS(CI, NH3) m/e 286 (base, M+H+). HRMS(CI, NH3) m/e Calc'd for (M+H+): 286.1266. Found: 286.1259.

Workup

  1. customPurified by flash chromatography
  2. washeluting with 1:1 EtOAc/hexane

Sources & evidence

ORD record
ord-c522d145f2db4ae4b0e02405e73a9124
Source dataset
uspto-grants-2001_05
Patent number
US06239143B1

Reaction notes

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