1-(2-Hydroxyethyl)piperazine → (S)-2-(4-((1,2,3,4-Tetrahydroisoquinolin-3-yl)methyl)piperazin-1-yl)ethanol

HRID 528875Notes

Reaction equation

HRID 528875 reaction equation
[CH:1]([C@@H:3]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][N:4]1C(OC(C)(C)C)=O)=O.[N:20]1([CH2:26][CH2:27][OH:28])[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1>>[CH2:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH2:12][C@@H:3]([CH2:1][N:23]2[CH2:24][CH2:25][N:20]([CH2:26][CH2:27][OH:28])[CH2:21][CH2:22]2)[NH:4]1

Participants

3

Reactant 2

HCID 76771-(2-Hydroxyethyl)piperazineHCID 22861260(S)-tert-Butyl 3-formyl-3,4-dihydroisoquinoline-2(1H)-carboxylate

Product 1

HCID 86718899(S)-2-(4-((1,2,3,4-Tetrahydroisoquinolin-3-yl)methyl)piperazin-1-yl)ethanol

Procedure

Following a procedure analogous to that for the synthesis of Example 107, (S)-tert-butyl 3-formyl-3,4-dihydroisoquinoline-2(1H)-carboxylate (58 mg, 0.22 mmol) and 2-(piperazin-1-yl)ethanol (33 μL, 0.267 mmol) provided a crude oil which was used without purification in the preparation of Example 115. MS(ESI+) m/z 276.2 (M+H)+.

Workup

  1. customprovided a crude oil which
  2. customwas used without purification in the preparation of Example 115

Sources & evidence

ORD record
ord-ebace1745cf841b69107285fb44eb4ca
Source dataset
uspto-grants-2016_05
Patent number
US09346795B2

Reaction notes

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