Acetyl chloride → 2-(4-Acetamidophenyl)-6-methoxy-1-[4-(phenylmethoxy)benzyl]-1,2,3,4-tetrahydroisoquinoline

HRID 2304658Notes

Reaction equation

HRID 2304658 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:17][CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([O:18][CH3:19])[CH:14]=3)[CH:9]2[CH2:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[CH:23][CH:22]=2)=[CH:4][CH:3]=1.[C:35](Cl)(=[O:37])[CH3:36]>C(Cl)Cl>[C:35]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:17][CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([O:18][CH3:19])[CH:14]=3)[CH:9]2[CH2:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][CH2:28][C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)=[CH:23][CH:22]=2)=[CH:4][CH:3]=1)(=[O:37])[CH3:36]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 234407492-(4-Aminophenyl)-6-methoxy-1-[4-(phenylmethoxy)benzyl]-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 234408602-(4-Acetamidophenyl)-6-methoxy-1-[4-(phenylmethoxy)benzyl]-1,2,3,4-tetrahydroisoquinolineYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-(4-aminophenyl)-6-methoxy-1-[4-(phenylmethoxy)benzyl]-1,2,3,4-tetrahydroisoquinoline (0.205 g, 0.46 mmol) and TEA (0.060 g, 0.6 mmol) in 1 mL of CH2Cl2 at 0° C. was treated with acetyl chloride (0.043 g, 0.55 mmol). The reaction mixture was warmed to room temperature and stirred for 3 hours. The reaction was quenched by the addition of saturated aqueous NaHCO3 (0.5 mL). The organic layer was separated and the aqueous layer was extracted with CH2Cl2 (3×2 mL). The combined organic layer was dried over MgSO4 then concentrated. The crude product was purified by column chromatography to provide the title compound (0.195 g, 87% yield). ES-MS, (m/z) 493 [M+H]+.

Workup

  1. customThe reaction was quenched by the addition of saturated aqueous NaHCO3 (0.5 mL)
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with CH2Cl2 (3×2 mL)
  4. dry with materialThe combined organic layer was dried over MgSO4
  5. concentrationthen concentrated
  6. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-662332ca10d4416ebe9217fe85c52e4b
Source dataset
uspto-grants-2002_08
Patent number
US06436923B1

Reaction notes

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