Potassium Carbonate → HCID 68213446, compound

HRID 1186248Notes

Reaction equation

HRID 1186248 reaction equation
Cl.[NH2:2][CH2:3][C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=1.[CH3:14][O:15][C:16]1[CH:17]=[CH:18][CH:19]=[C:20]2[C:25]=1[CH2:24][C:23](=O)[CH2:22][CH2:21]2.C(N(CC)C(C)C)(C)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])[O-].[K+].[K+]>ClCCl.O.C(O)(=O)C>[CH3:14][O:15][C:16]1[CH:17]=[CH:18][CH:19]=[C:20]2[C:25]=1[CH2:24][CH:23]([NH:2][CH2:3][C:4]1[CH:5]=[CH:6][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:12][CH:13]=1)[CH2:22][CH2:21]2

Participants

9

Reactant 5

HCID 11430Potassium CarbonateHCID 81531DiisopropylethylamineHCID 2729253Methyl 4-(aminomethyl)benzoate hydrochlorideHCID 41360218-Methoxy-2-tetraloneHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 68213446HCID 68213446, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

15 g (74.4 mmol) of methyl 4-(aminomethyl)benzoate hydrochloride, 13.8 g (78.1 mmol) of 8-methoxy-3,4-dihydronaphthalen-2(1H)-one [for the preparation, see WO 2005/012291-A1, Example 45], 14.3 ml (81.8 mmol) of N,N-diisopropylethylamine, 4.7 ml of acetic acid and 20.5 g (96.7 mmol) of sodium triacetoxyborohydride were suspended in 600 ml of dichloromethane and stirred at RT overnight. The reaction mixture was then concentrated and the residue was stirred with ethyl acetate and water at RT for 1 h. The resulting precipitated solid was filtered off with suction. The filtrate phases were separated and the aqueous phase was extracted twice with ethyl acetate. The combined organic phases were dried and concentrated. The solid obtained above (18.2 g) and the residue of the organic phase (12.9 g) were combined and once more stirred in a mixture of dichloromethane, water and saturated potassium carbonate solution (pH 12) until everything had gone into solution. The organic phase was then separated off, dried and concentrated. The title compound was obtained in the form of the residue.

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. stirringthe residue was stirred with ethyl acetate and water at RT for 1 h
  3. customThe resulting precipitated solid
  4. filtrationwas filtered off with suction
  5. customThe filtrate phases were separated
  6. extractionthe aqueous phase was extracted twice with ethyl acetate
  7. customThe combined organic phases were dried
  8. concentrationconcentrated
  9. customThe solid obtained above (18.2 g)
  10. customThe organic phase was then separated off
  11. customdried
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-5a493ed340f741c4ad4208a84159db5f
Source dataset
uspto-grants-2014_03
Patent number
US08673903B2

Reaction notes

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