Hydrochloric Acid → 6-Methoxy-2-capryloyl-1,2,3,4-tetrahydroisoquinoline

HRID 2413494

Reaction equation

HRID 2413494 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][NH:8][CH2:7][CH2:6]2.[C:13](Cl)(=[O:21])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].Cl.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl.O.C(N(CC)CC)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][N:8]([C:13](=[O:21])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH2:7][CH2:6]2

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8124Octanoyl chlorideHCID 10340Sodium CarbonateHCID 393566-Methoxy-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 201558096-Methoxy-2-capryloyl-1,2,3,4-tetrahydroisoquinoline

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

4.0 g of 6-methoxy-1,2,3,4-tetrahydroisoquinoline and 3.5 ml of triethylamine in 50 ml of methylene chloride are initially introduced, and a solution of 4.0 g of octanoyl chloride in 10 ml of methylene chloride is added dropwise with stirring and cooling. The mixture is stirred at room temperature for 1 hour, then shaken with 1N hydrochloric acid, sodium carbonate solution and water, and the organic phase is dried over magnesium sulfate and evaporated in a rotary evaporator. The crude product (6.7 g of colorless oil) is reacted further without purification.

Workup

  1. temperaturecooling
  2. stirringThe mixture is stirred at room temperature for 1 hour
  3. dry with materialthe organic phase is dried over magnesium sulfate
  4. customevaporated in a rotary evaporator
  5. customThe crude product (6.7 g of colorless oil) is reacted further without purification

Sources & evidence

ORD record
ord-4634ee63f25b4374b64a956d86e950da
Source dataset
uspto-grants-1988_01
Patent number
US04717724

Linked notes

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