Trityl chloride → HCID 54516501, compound

HRID 1757475Notes

Reaction equation

HRID 1757475 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([CH:10]([C:19]#[N:20])[CH2:11][CH2:12][CH:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[CH:6]=[CH:7][C:8]=1[Cl:9].[C:21](Cl)([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(N(CC)CC)C>C(Cl)Cl>[Cl:2][C:3]1[CH:4]=[C:5]([CH:10]([C:19]#[N:20])[CH2:11][CH2:12][CH:13]2[CH2:14][CH2:15][N:16]([C:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)([C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)[C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[CH2:17][CH2:18]2)[CH:6]=[CH:7][C:8]=1[Cl:9]

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 67583427HCID 67583427, compound

Product 1

HCID 54516501HCID 54516501, compoundYield 96.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

25 g of 1-(3,4-dichlorophenyl)-3-(4-piperidinyl)-1-cyanopropane hydrochloride (Example 1B) are dissolved in 400 ml of CH2Cl2. 22 g of trityl chloride and 21 ml of triethylamine are added dropwise to the solution. The reaction mixture is left for 2 hours without stirring, and washed successively with H2O, an aqueous solution buffered to pH=2, and a solution saturated with NaCl. It is dried over MgSO4 and evaporated. The residue is chromatographed on silica gel, eluent: heptane/ethyl acetate 9:1 (v/v). 39 g of oil are obtained.

Workup

  1. washwashed successively with H2O
  2. dry with materialIt is dried over MgSO4
  3. customevaporated
  4. customThe residue is chromatographed on silica gel, eluent

Sources & evidence

ORD record
ord-625ae3b035a14290afece76e17d62bd5
Source dataset
uspto-grants-1995_08
Patent number
US05446052

Reaction notes

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