Diethyl (2-aminoethyl)phosphonate → Diethyl 2-(3-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)phenylsulfonamido)ethylphosphonate

HRID 45637

Reaction equation

HRID 45637 reaction equation
[NH2:1][CH2:2][CH2:3][P:4](=[O:11])([O:8][CH2:9][CH3:10])[O:5][CH2:6][CH3:7].[Cl:12][C:13]1[CH:14]=[C:15]2[C:20](=[C:21]([Cl:23])[CH:22]=1)[CH2:19][N:18]([CH3:24])[CH2:17][CH:16]2[C:25]1[CH:26]=[C:27]([S:31](Cl)(=[O:33])=[O:32])[CH:28]=[CH:29][CH:30]=1>ClCCl>[Cl:12][C:13]1[CH:14]=[C:15]2[C:20](=[C:21]([Cl:23])[CH:22]=1)[CH2:19][N:18]([CH3:24])[CH2:17][CH:16]2[C:25]1[CH:26]=[C:27]([S:31]([NH:1][CH2:2][CH2:3][P:4](=[O:11])([O:5][CH2:6][CH3:7])[O:8][CH2:9][CH3:10])(=[O:33])=[O:32])[CH:28]=[CH:29][CH:30]=1

Participants

4

Reactant 2

HCID 2733596Diethyl (2-aminoethyl)phosphonateHCID 866723303-(6,8-Dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)benzene-1-sulfonyl chloride

Product 1

HCID 86672329Diethyl 2-(3-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)phenylsulfonamido)ethylphosphonateYield 24%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a 50-mL round-bottom flask, was placed a solution of diethyl 2-aminoethylphosphonate (100 mg, 0.55 mmol, 1.00 equiv) in dichloromethane (10 mL) with TEA (220 mg, 2.18 mmol, 3.94 equiv). This was followed by the addition of 3-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)benzene-1-sulfonyl chloride (300 mg, 0.60 mmol, 1.08 equiv, 78%) in several batches. The resulting solution was stirred for 2 h at room temperature. The reaction progress was monitored by LCMS. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with dichloromethane:methanol (50:1). This resulted in 0.07 g (24%) of the title compound as a colorless oil.

Workup

  1. customInto a 50-mL round-bottom flask, was placed
  2. concentrationThe resulting mixture was concentrated under vacuum

Sources & evidence

ORD record
ord-1038b05b2c15476fa1869a4b884baaf6
Source dataset
uspto-grants-2013_09
Patent number
US08541448B2

Linked notes

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