Hydrochloric Acid → HCID 19085439, compound

HRID 962446Notes

Reaction equation

HRID 962446 reaction equation
[N:1]1([CH2:7][CH2:8][CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:15]1([O:21][CH2:22][CH2:23]Br)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[ClH:25].C(=O)(O)[O-].[Na+]>CCOCC.CN(C=O)C.C(N(CC)CC)C>[ClH:25].[ClH:25].[O:21]([CH2:22][CH2:23][N:12]1[CH2:13][CH2:14][CH:9]([CH2:8][CH2:7][N:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)[CH2:10][CH2:11]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

8

Reactant 4

HCID 313Hydrochloric Acid2×HCID 68526Benzene, (2-bromoethoxy)-HCID 2962921-[2-(Piperidin-4-yl)ethyl]piperidineHCID 516892Sodium Bicarbonate

Product 1

HCID 19085439HCID 19085439, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 4-(2-piperidinoethyl)piperidine (3.27 g), 2-bromoethyl phenyl ether (3.35 g), triethylamine (2.3 ml) and DMF (50 ml) was heated on a steam bath for 16 hours. The mixture was worked up as described in Example 16. The crude solid hydrochloride was treated with sodium bicarbonate solution and the mixture extracted with dichloromethane to give the free base which was purified by flash chromatography on silica using methanol/triethylamine, 99:1 as the mobile phase. The oil obtained was dissolved in ether and acidified with ethereal hydrogen chloride to give 1-(2-phenoxyethyl)-4-(2-piperidinoethyl)piperidine dihydrochloride, m.p. 285° C.

Workup

  1. temperaturewas heated on a steam bath for 16 hours
  2. extractionthe mixture extracted with dichloromethane
  3. customto give the free base which
  4. customwas purified by flash chromatography on silica
  5. customThe oil obtained

Sources & evidence

ORD record
ord-5404721bece540f397369fede4e85c5f
Source dataset
uspto-grants-1998_06
Patent number
US05760035

Reaction notes

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