Dichloromethane → HCID 18663592, compound

HRID 1956587Notes

Reaction equation

HRID 1956587 reaction equation
C(OC(=O)[N:7]([CH2:11][C:12]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[O:16][C:15]2[CH:23]=[CH:24][CH:25]=[CH:26][C:14]=2[CH:13]=1)[CH2:8][C:9]#[CH:10])(C)(C)C.CS(O)(=O)=O.[OH-].[Na+].[Cl:35]CCl>O1CCOCC1>[ClH:35].[CH:26]1[C:14]2[CH:13]=[C:12]([CH2:11][NH:7][CH2:8][C:9]#[CH:10])[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[O:16][C:15]=2[CH:23]=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6395Methanesulfonic AcidHCID 14798Sodium HydroxideHCID 86752907HCID 86752907, compound

Product 1

HCID 18663592HCID 18663592, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 1.1 g (3.044 mmol) of N-(dibenz[b,f]oxepin-10-ylmethyl-prop-2-ynyl-carbamic acid tert-butyl ester and 1.45 ml of methanesulfonic acid in 1 ml of dioxane and 9 ml of dichloromethane is stirred for 1 hour at room temperature, 2N sodium hydroxide solution is added and the mixture is extracted 2× with dichloromethane. The organic phase is concentrated using a rotary evaporator, taken up in ethyl acetate and extracted 3× with 1N hydrochloric acid, and the aqueous phase is rendered basic with potassium hydroxide pellets, extracted 3× with dichloromethane, dried over sodium sulfate and concentrated. The crude light-brown oil is dissolved in 2N ethereal hydrochloric acid and concentrated. The crude hydrochloride (beige crystals) is recrystallised from ethyl acetate/methanol. 386 mg (1.30 mmol)=42% of N-(dibenz[b,f]oxepin-10-ylmethyl)-N-prop-2-ynylamine hydrochloride alias 10-propargylaminomethyldibenz[b,f]oxepine hydrochloride are obtained in the form of white crystals; melting point: 181°-183° C.; MS: 261 (M+, free base), 222,181, 165, 152.

Workup

  1. extractionthe mixture is extracted 2× with dichloromethane
  2. concentrationThe organic phase is concentrated
  3. customa rotary evaporator
  4. extractionextracted 3× with 1N hydrochloric acid
  5. extractionextracted 3× with dichloromethane
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. dissolutionThe crude light-brown oil is dissolved in 2N ethereal hydrochloric acid
  9. concentrationconcentrated
  10. customThe crude hydrochloride (beige crystals) is recrystallised from ethyl acetate/methanol

Sources & evidence

ORD record
ord-885f8d8eb3da4a9dba002cb81e6a938e
Source dataset
uspto-grants-1998_07
Patent number
US05780501

Reaction notes

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