Dichloromethane → HCID 68888976, compound

HRID 1760600Notes

Reaction equation

HRID 1760600 reaction equation
C(OC([N:8]1[CH2:22][CH:21]([CH3:23])[N:11]2[C:12]3[C:13]([C:19]#[N:20])=[CH:14][CH:15]=[CH:16][C:17]=3[CH:18]=[C:10]2[CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.[Cl:31]CCl>>[ClH:31].[CH3:23][C@H:21]1[N:11]2[C:12]3[C:17]([CH:18]=[C:10]2[CH2:9][NH:8][CH2:22]1)=[CH:16][CH:15]=[CH:14][C:13]=3[C:19]#[N:20]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 68890354HCID 68890354, compound

Product 1

HCID 68888976HCID 68888976, compound

Procedure

A solution of 80.0 mg (0.26 mmol) 6-cyano-4-methyl-3,4-dihydro-1H-pyrazino[1,2-a]indole-2-carboxylic acid tert-butyl ester in 3 ml dichloromethane was cooled to 0° C. and treated dropwise with 1 ml trifluoroacetic acid. After 30 min. the solution was concentrated at a rotary evaporator and the residue was chromatographed on silica gel (0.032-0.063 mm) with ethyl acetate: methanol: ammonia (9:1:0.1) as eluant. The product was dissolved in 3 ml diethyl ether and treated dropwise with 43 μl of a 6M hydrochloric acid solution in ethyl acetate. The suspension was filtered and the solid was dried under high vacuum to give the desired compound as light yellow crystals. EI-MS:: m/e=211.2 ([M]).

Workup

  1. concentrationAfter 30 min. the solution was concentrated at a rotary evaporator
  2. customthe residue was chromatographed on silica gel (0.032-0.063 mm) with ethyl acetate: methanol: ammonia (9:1:0.1) as eluant
  3. dissolutionThe product was dissolved in 3 ml diethyl ether
  4. additiontreated dropwise with 43 μl of a 6M hydrochloric acid solution in ethyl acetate
  5. filtrationThe suspension was filtered
  6. customthe solid was dried under high vacuum

Sources & evidence

ORD record
ord-6571a0ae324c4b9fa4ac6783d84352a0
Source dataset
uspto-grants-2005_01
Patent number
US06844345B2

Reaction notes

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