Diethyl Ether → HCID 19784348, compound

HRID 257090Notes

Reaction equation

HRID 257090 reaction equation
C(O)(=O)/C=C/C(O)=O.[C:9]([C:12]1[CH:17]=[CH:16][C:15]([N:18]2[CH2:23][CH2:22][CH:21]([N:24]([CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH3:25])[CH2:20][CH2:19]2)=[CH:14][CH:13]=1)(=[O:11])[CH3:10].[Br:33]Br.CCOCC>C(O)(=O)C>[BrH:33].[C:9]([C:12]1[CH:13]=[CH:14][C:15]([N:18]2[CH2:19][CH2:20][CH:21]([N:24]([CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH3:25])[CH2:22][CH2:23]2)=[C:16]([Br:33])[CH:17]=1)(=[O:11])[CH3:10]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 24408BromineHCID 19784345HCID 19784345, compound

Product 1

HCID 19784348HCID 19784348, compoundYield 183.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

2.5 g (7.9 mmol)of the product from Example 17 were dissolved in 50 ml of glacial acetic acid and, at room temperature, 1.26 g (7.9 mmol) of bromine dissolved in 10 ml of glacial acetic acid were added dropwise. The mixture was stirred for 4 hours, after which ether was added, whereupon crystals slowly separated out. The crystals were filtered off and washed with ether. 3.5 g of 1-(4-acetyl-2-bromophenyl)-4-(N-benzyl-N-methylamino)piperidine hydrobromide were obtained. Melting point 201°-202° C.

Workup

  1. additionwere added dropwise
  2. customslowly separated out
  3. filtrationThe crystals were filtered off
  4. washwashed with ether

Sources & evidence

ORD record
ord-1e3f0b5d5f664442848a8eac2c419f1e
Source dataset
uspto-grants-1993_11
Patent number
US05260318

Reaction notes

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