Acetyl chloride → HCID 14836551, compound

HRID 1614267Notes

Reaction equation

HRID 1614267 reaction equation
Cl.Cl.[NH2:3][C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH2:6][CH2:7][CH:8]([N:14]([CH2:18][CH2:19][CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:15][CH2:16][CH3:17])[CH2:9]2.C(N(CC)CC)C.[C:35](Cl)(=[O:37])[CH3:36]>C(Cl)Cl>[C:35]([NH:3][C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH2:6][CH2:7][CH:8]([N:14]([CH2:18][CH2:19][CH2:20][CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[CH2:15][CH2:16][CH3:17])[CH2:9]2)(=[O:37])[CH3:36]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 19773355HCID 19773355, compound

Product 1

HCID 14836551HCID 14836551, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

0.90 g (0.0022 mol) of 5-amino-2-[N-(4-phenylbutyl)-N-n-propyl-amino]-tetraline-dihydrochloride (Example 4.5.4) and 1.00 g (0.0099 mol) of triethylamine are mixed with 15 ml of absolute methylene chloride with stirring and cooling with ice and 0.20 g (2.55 mmol) of acetylchloride in 5 ml of absolute methylene chloride are added. After 3 hours at ambient temperature or 30 minutes refluxing, the mixture is extracted three times with 5 ml of water, dried with sodium sulphate and concentrated by rotary evaporation, finally at 80° C. under a complete water-jet vacuum. The residue is crystallised from diethylether/petroleum ether.

Workup

  1. additionare added
  2. temperature30 minutes refluxing
  3. extractionthe mixture is extracted three times with 5 ml of water
  4. dry with materialdried with sodium sulphate
  5. concentrationconcentrated by rotary evaporation, finally at 80° C. under a complete water-jet vacuum
  6. customThe residue is crystallised from diethylether/petroleum ether

Sources & evidence

ORD record
ord-1673b288e8d14a90b3033d5be1be4be8
Source dataset
uspto-grants-1993_03
Patent number
US05196454

Reaction notes

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