1,2,3,4-Tetrahydroisoquinoline → HCID 86665957, compound

HRID 1024728Notes

Reaction equation

HRID 1024728 reaction equation
[C:1]([C:3]1[CH:27]=[CH:26][C:6]([O:7][C:8]2[CH:9]=[C:10]([CH:14]=[C:15]([O:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]#[N:25])=[CH:20][CH:19]=3)[CH:16]=2)[C:11]([OH:13])=O)=[CH:5][CH:4]=1)#[N:2].[CH2:28]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH2:31][CH2:30][NH:29]1>>[CH2:28]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH2:31][CH2:30][N:29]1[C:11]([C:10]1[CH:9]=[C:8]([O:7][C:6]2[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:27][CH:26]=2)[CH:16]=[C:15]([O:17][C:18]2[CH:19]=[CH:20][C:21]([C:24]#[N:25])=[CH:22][CH:23]=2)[CH:14]=1)=[O:13]

Participants

3

Reactant 2

HCID 70461,2,3,4-TetrahydroisoquinolineHCID 66818818HCID 66818818, compound

Product 1

HCID 86665957HCID 86665957, compoundYield 85.2%

Procedure

Following the procedure of Example 5(c) 3,5-bis-(4-cyano-phenoxy)-benzoic acid 0.8 g (2.24 mmol) and 1,2,3,4-tetrahydro-isoquinoline (0.3 g, 2.26 mmol) were used to afford 0.9 g of the required product. 1H NMR (DMSO-d6): δ 2.82 (2H, m), 3.58 (1H, m), 3.80 (1H, m), 4.08 (1H, m), 4.74 (1H, m), 7.10 (3H, m), 7.20 (4H, m), 7.28 (4H, d), 7.90 (2H, d).

Sources & evidence

ORD record
ord-bf3984f1b8954391b296448d577b579d
Source dataset
uspto-grants-2014_05
Patent number
US08722930B2

Reaction notes

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