1-Methylpiperazine → (S)-3-((4-Methylpiperazin-1-yl)methyl)-1,2,3,4-tetrahydroisoquinoline

HRID 528873Notes

Reaction equation

HRID 528873 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.[CH3:20][N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1>>[CH3:20][N:21]1[CH2:26][CH2:25][N:24]([CH2:1][C@@H:3]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH2:5][NH:4]2)[CH2:23][CH2:22]1

Participants

3

Reactant 2

HCID 531671-MethylpiperazineHCID 22861260(S)-tert-Butyl 3-formyl-3,4-dihydroisoquinoline-2(1H)-carboxylate

Product 1

HCID 28597071(S)-3-((4-Methylpiperazin-1-yl)methyl)-1,2,3,4-tetrahydroisoquinoline

Procedure

Following a procedure analogous to that for the synthesis of Example 107, (S)-tert-butyl 3-formyl-3,4-dihydroisoquinoline-2(1H)-carboxylate (57 mg, 0.22 mmol) and 1-methylpiperazine (26 mg, 0.26 mmol) provided a crude oil which was used without purification in the preparation of Example 112. MS(ESI+) m/z 246.1 (M+H)+.

Workup

  1. customprovided a crude oil which
  2. customwas used without purification in the preparation of Example 112

Sources & evidence

ORD record
ord-530f229809924141af51c832dc34ab9d
Source dataset
uspto-grants-2016_05
Patent number
US09346795B2

Reaction notes

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