Hydrochloric Acid → HCID 18962082, compound

HRID 2399394Notes

Reaction equation

HRID 2399394 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:14]#[CH:15])[CH:5]=[CH:6][C:7]=1[CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.[CH2:16]=O.[CH3:18][NH:19][CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1.Cl.[OH-].[Na+]>O1CCOCC1.CCOCC.O>[ClH:1].[CH:20]1([N:19]([CH2:16][C:15]#[C:14][C:4]2[CH:5]=[CH:6][C:7]([CH:8]3[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]3)=[C:2]([Cl:1])[CH:3]=2)[CH3:18])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 7514N-MethylcyclohexylamineHCID 14798Sodium HydroxideHCID 101768033-chloro-4-cyclohexyl-1-ethynylbenzene

Product 1

HCID 18962082HCID 18962082, compoundYield 58.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution containing 16.4 g of 3-chloro-4-cyclohexyl-1-ethynylbenzene, prepared above, in 30 ml of dioxane, 4.5 g of paraformaldehyde and 0.15 g of cuprous chloride is heated to 60° C. and 9.3 g of N-methyl-N-cyclohexylamine are then added over half an hour. The temperature is kept at 60° C. for 1 hour. When the reaction is complete, the cooled mixture is diluted with ether and treated with water and then with a dilute solution of hydrochloric acid. The acid solution is then rendered alkaline with a dilute solution of sodium hydroxide and extracted with ether. The organic phase is dried over sodium sulfate and then concentrated. The hydrochloride is prepared from the crude base, washed with water and then crystallized twice from acetonitrile to give 8.4 g of the expected compound. M.p.: 75° C.

Workup

  1. extractionextracted with ether
  2. dry with materialThe organic phase is dried over sodium sulfate
  3. concentrationconcentrated
  4. customThe hydrochloride is prepared from the crude base
  5. washwashed with water
  6. customcrystallized twice from acetonitrile

Sources & evidence

ORD record
ord-bd6160a57f374714b8f50bb83ea30861
Source dataset
uspto-grants-1995_09
Patent number
US05449693

Reaction notes

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