Chloroacetyl chloride → HCID 59396702, compound

HRID 2383010Notes

Reaction equation

HRID 2383010 reaction equation
C([C@@H]([C@H](C(O)=O)O)O)(O)=O.[CH:11]1([C@@H:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:20][CH2:19][NH:18]2)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.C(=O)(O)[O-].[Na+].[Cl:32][CH2:33][C:34](Cl)=[O:35]>CCOC(C)=O>[Cl:32][CH2:33][C:34]([N:18]1[CH2:19][CH2:20][C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[C@H:17]1[CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1)=[O:35]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 516892Sodium BicarbonateHCID 86643132HCID 86643132, compound

Product 1

HCID 59396702HCID 59396702, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

(1R)-1-cyclohexyl-1,2,3,4-tetrahydroisoquinoline (L)-tartrate (520 mg) was dissolved in EtOAc (10 mL) and saturated aqueous sodium bicarbonate (10 mL) was added thereto. Under ice-cooling, a solution of chloroacetyl chloride (0.14 mL) in EtOAc (5 mL) was added dropwise to the reaction liquid over 5 minutes, followed by stirring at room temperature for 1 hour. The reaction liquid was extracted with EtOAc and dried over magnesium sulfate to obtain (1R)-2-(chloroacetyl)-1-cyclohexyl-1,2,3,4-tetrahydroisoquinoline (415 mg).

Workup

  1. temperatureUnder ice-cooling
  2. customThe reaction liquid
  3. extractionwas extracted with EtOAc
  4. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-1556d630cd1d4a73b9df81ef69955ab9
Source dataset
uspto-grants-2012_09
Patent number
US08263607B2

Reaction notes

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