Triethylamine → HCID 53700015, compound

HRID 2291735Notes

Reaction equation

HRID 2291735 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)=[C:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:4][CH:3]=1.Br[CH2:23][CH2:24][CH2:25][O:26][C:27]([C:29]12[CH2:38][CH:33]3[CH2:34][CH:35]([CH2:37][CH:31]([CH2:32]3)[CH2:30]1)[CH2:36]2)=[O:28].C(N(CC)CC)C>C(Cl)Cl>[F:21][C:18]1[CH:17]=[CH:16][C:15]([C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[C:9]2[CH2:14][CH2:13][N:12]([CH2:23][CH2:24][CH2:25][O:26][C:27]([C:29]34[CH2:30][CH:31]5[CH2:32][CH:33]([CH2:34][CH:35]([CH2:37]5)[CH2:36]3)[CH2:38]4)=[O:28])[CH2:11][CH2:10]2)=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27244364-(Bis(4-fluorophenyl)methylene)piperidineHCID 14373539HCID 14373539, compound

Product 1

HCID 53700015HCID 53700015, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3-bromopropanol (5.5 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, 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 bromopropyl ester. The title compound was prepared by stirring 4-[bis(4-fluorophenyl)-methylene]piperidine (2 g, 0.07 mol), adamantane-1-carboxylic acid bromo-propyl ester (2.1 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 =0.7 in 30% ethanol/ethylacetate system) was separated and converted to the hydrochloride salt (0.6 g, 16% yield), mp. 267°-269° C.

Workup

  1. washThe methylene chloride was washed with water
  2. dry with materialdried (anhydrous Na2SO4)
  3. customremoved under reduced pressure
  4. customthe desired product (TLC Rf =0.7 in 30% ethanol/ethylacetate system) was separated

Sources & evidence

ORD record
ord-ed97d6615e744bdc9b28d3e7f371fc9e
Source dataset
uspto-grants-1989_01
Patent number
US04797489

Reaction notes

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