Hydrochloric Acid → HCID 22129669, compound

HRID 1857655Notes

Reaction equation

HRID 1857655 reaction equation
Cl.[OH:2][C:3]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:8][CH2:7][N:6]([CH:9]([C:18]#[N:19])[C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([Cl:17])[CH:11]=2)[CH2:5][CH2:4]1.C[Si](C#N)(C)C.Cl[C:33]1[CH:34]=[C:35](C=[CH:39][C:40]=1Cl)[CH:36]=[O:37].O[C:43]1(C2C=CC=CC=2)CCNCC1.Cl.C[CH2:57][O:58][CH2:59][CH3:60].CCCCCC.C(O)C>ClCCl.CO.[I-].[Zn+2].[I-].CCOCC>[ClH:16].[Cl:17][C:12]1[CH:11]=[C:10]([CH:9]([N:6]2[CH2:5][CH2:4][C:3]([OH:2])([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:8][CH2:7]2)[CH2:18][N:19]([CH3:43])[C:36](=[O:37])[CH2:35][C:34]2[CH:33]=[CH:40][CH:39]=[CH:60][C:59]=2[O:58][CH3:57])[CH:15]=[CH:14][C:13]=1[Cl:16]

Participants

11

Reactant 6

HCID 313Hydrochloric AcidHCID 227103,4-DichlorobenzaldehydeHCID 82115Trimethylsilyl cyanideHCID 963874-Phenylpiperidin-4-olHCID 17821937HCID 17821937, compoundHCID 22129667HCID 22129667, compound

Product 1

HCID 22129669HCID 22129669, compound

Reagents, catalysts & solvents 4

HCID 9883512zinc(II)iodideCatalystHCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
23 °C

Procedure

α-(4-Hydroxy-4-phenylpiperidino)-3,4-dichlorobenzyl cyanide hydrochloride salt. Trimethylsilylcyanide (2.02 g) and catalytic zinc iodide were added to a solution of 3,4-dichlorobenzaldehyde (2.86 g) in dichloromethane (45 mL) at 23° C. The reaction was stirred at 23° C. for 20 minutes and treated with a solution of 4-hydroxy-4-phenylpiperdine (2.89 g) in methanol (20 mL). The reaction was refluxed for 2.5 hours and stirred 18 hours at 23° C. The reaction was cooled in an ice bath and treated with hydrochloric acid (g)/ether (pH=1 to 2). The reaction was stirred at 23° C. for 1 hour and evaporated give to a tan oil. Trituration of the oil with ether:hexane:ethanol (1:1:1) gave the title compound as a pale yellow solid (5.09 g) which was used directly in subsequent reactions; MS: m/z=361(M+1).

Workup

  1. temperatureThe reaction was refluxed for 2.5 hours
  2. stirringstirred 18 hours at 23° C
  3. temperatureThe reaction was cooled in an ice bath
  4. stirringThe reaction was stirred at 23° C. for 1 hour
  5. customevaporated
  6. customgive to a tan oil

Sources & evidence

ORD record
ord-3a4d19bf5dff46f1a4892e386e51badb
Source dataset
uspto-grants-2000_11
Patent number
US06147083

Reaction notes

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