1,2,3,4-Tetrahydroisoquinoline → HCID 9905998, compound

HRID 1978906Notes

Reaction equation

HRID 1978906 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][NH:2]1.[Li]CCCC.Cl[CH2:17][CH2:18][CH2:19][C:20]1([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)[O:24][CH2:23][CH2:22][O:21]1>>[F:31][C:28]1[CH:27]=[CH:26][C:25]([C:20]2([CH2:19][CH2:18][CH2:17][N:2]3[CH2:3][CH2:4][C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[CH2:1]3)[O:21][CH2:22][CH2:23][O:24]2)=[CH:30][CH:29]=1

Participants

4

Reactant 3

HCID 70461,2,3,4-TetrahydroisoquinolineHCID 27237782-(3-Chloropropyl)-2-(4-fluorophenyl)-1,3-dioxolaneHCID 178418339Butyllithium

Product 1

HCID 9905998HCID 9905998, compoundYield 16%

Procedure

1,2,3,4-Tetrahydroisoquinoline, n-BuLi, and 2-(3-chloropropyl)-2-(4-fluorophenyl)-1,3-dioxolane were allowed to react under conditions analogous to Example 1, Method C. Flash chromatographic purification provided 4A (16% yield) as a yellow oil. 1H NMR(300 MHz, CDCl3, δ): 7.44-7.39 (m, 2H), 7.15-6.98 (m, 6H), 4.08-3.96 (m, 2H), 3.83-3.71 (m, 2H), 3.57 (s, 2H), 2.87 (t, 2H, J=6 Hz), 2.67 (t, 2H, J=6 Hz), 2.47 (t, 2H, J=7 Hz), 1.96-1.91 (m, 2H), 1.69-1.59 (m, 2H).

Workup

  1. customto react under conditions analogous to Example 1, Method C
  2. custompurification

Sources & evidence

ORD record
ord-cec837c08e81406493d5bd46bd300c38
Source dataset
uspto-grants-2001_05
Patent number
US06239143B1

Reaction notes

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