Triethylamine → HCID 54272040, compound

HRID 2291737Notes

Reaction equation

HRID 2291737 reaction equation
BrCCO.C12(C(Cl)=O)CC3CC(CC(C3)C1)C2.C(N(CC)CC)C.Br[CH2:26][CH2:27][O:28][C:29]([C:31]12[CH2:40][CH:35]3[CH2:36][CH:37]([CH2:39][CH:33]([CH2:34]3)[CH2:32]1)[CH2:38]2)=[O:30].[F:41][C:42]1[CH:47]=[CH:46][C:45]([C:48]([C:55]2[CH:60]=[CH:59][C:58]([F:61])=[CH:57][CH:56]=2)=[C:49]2[CH2:54][CH2:53][NH:52][CH2:51][CH2:50]2)=[CH:44][CH:43]=1>C(Cl)Cl>[F:61][C:58]1[CH:59]=[CH:60][C:55]([C:48]([C:45]2[CH:44]=[CH:43][C:42]([F:41])=[CH:47][CH:46]=2)=[C:49]2[CH2:54][CH2:53][N:52]([CH2:26][CH2:27][O:28][C:29]([C:31]34[CH2:40][CH:35]5[CH2:36][CH:37]([CH2:39][CH:33]([CH2:34]5)[CH2:32]3)[CH2:38]4)=[O:30])[CH2:51][CH2:50]2)=[CH:56][CH:57]=1

Participants

7

Reactant 5

HCID 8471Triethylamine2×HCID 108982-BromoethanolHCID 989151-Adamantanecarbonyl chlorideHCID 27244364-(Bis(4-fluorophenyl)methylene)piperidineHCID 10660921HCID 10660921, compound2×

Product 1

HCID 54272040HCID 54272040, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 2-bromoethanol (4.9 g., 0.04 mol) in 50 mL of methylene chloride, adamantane-1-carboxylic acid chloride (5.6 g., 0.02 mol) and triethylamine (4 g., 0.04 mol) were added. The reaction mixture was stirred at room temperature overnight and the methylene chloride was washed with water, dried over anhydrous Na2SO4 and removed under reduced pressure to afford 12 g. of the intermediate adamantane-1-carboxylic acid bromoethyl ester. The title compound was prepared by stirring 4-[bis(4-fluorophenyl)-methylene]piperidine (2 g., 0.07 mol), adamantane-1-carboxylic acid bromoethyl ester (2.0 g., 0.007 mol) and triethylamine (1 g., 0.01 mol) in 50 mL of CH2Cl2 for 24 hours. The methylene chloride was washed with water, dried (anhydrous Na2SO4) and removed under reduced pressure. The remaining residue was subjected to preparative HPLC over silica gel using ethylacetate as the eluent and the desired product (TLC Rf = 0.75 in 30% ethanol/ethylacetate system) was separated and converted to the hydrochloride salt with ethanolic HCl; mp. 249°-254° C.

Workup

  1. washthe methylene chloride was washed with water
  2. dry with materialdried over anhydrous Na2SO4
  3. customremoved under reduced pressure
  4. customto afford 12 g
  5. washThe methylene chloride was washed with water
  6. dry with materialdried (anhydrous Na2SO4)
  7. customremoved under reduced pressure
  8. customthe desired product (TLC Rf = 0.75 in 30% ethanol/ethylacetate system) was separated

Sources & evidence

ORD record
ord-fc7952648cce4a048e696f8544446ca0
Source dataset
uspto-grants-1989_01
Patent number
US04797489

Reaction notes

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