4-(Chloromethyl)phenyl isocyanate → 4-(7-(4-Methylphenyl)-1,2,3,4-tetrahydroisoquinolin-2-ylcarbonylamino)benzyl chloride

HRID 1169367Notes

Reaction equation

HRID 1169367 reaction equation
[Cl:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]=[C:10]=[O:11])=[CH:5][CH:4]=1.[CH3:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:28]=[C:27]3[C:22]([CH2:23][CH2:24][NH:25][CH2:26]3)=[CH:21][CH:20]=2)=[CH:15][CH:14]=1>O1CCCC1>[CH3:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]2[CH:28]=[C:27]3[C:22]([CH2:23][CH2:24][N:25]([C:10]([NH:9][C:6]4[CH:7]=[CH:8][C:3]([CH2:2][Cl:1])=[CH:4][CH:5]=4)=[O:11])[CH2:26]3)=[CH:21][CH:20]=2)=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 27333194-(Chloromethyl)phenyl isocyanateHCID 229900671,2,3,4-Tetrahydro-7-(4-methylphenyl)isoquinoline

Product 1

HCID 229900814-(7-(4-Methylphenyl)-1,2,3,4-tetrahydroisoquinolin-2-ylcarbonylamino)benzyl chlorideYield 93.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 4-(chloromethyl)phenylisocyanate (0.38 g) in tetrahydrofuran was added dropwise under ice cooling into a solution of 7-(4-methylphenyl)-1,2,3,4-tetrahydroisoquinoline (0.5 g) in tetrahydrofuran. The resulting mixture was stirred for one hour and was then evaporated to remove the solvent to obtain 4-(7-(4-methylphenyl)-1,2,3,4-tetrahydroisoquinolin-2-ylcarbonylamino)benzyl chloride (0.82 g) as colorless crystals.

Workup

  1. customwas then evaporated
  2. customto remove the solvent

Sources & evidence

ORD record
ord-237683ebf3194279b24bb9d864b4de6f
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

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