Hydrochloric Acid → HCID 178448123, compound

HRID 2060871Notes

Reaction equation

HRID 2060871 reaction equation
[CH:1]([CH:4]1[CH2:9][CH2:8][C:7](=O)[CH2:6][CH2:5]1)([CH3:3])[CH3:2].[CH2:11]([NH2:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[BH4-].[Na+].[ClH:21]>CO.O1CCOCC1.CCOCC.O>[ClH:21].[CH2:11]([NH:18][C@H:7]1[CH2:8][CH2:9][C@@H:4]([CH:1]([CH3:3])[CH3:2])[CH2:5][CH2:6]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 7504BenzylamineHCID 794884-IsopropylcyclohexanoneHCID 4311764Sodium borohydride

Product 1

HCID 178448123HCID 178448123, compound

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 4-isopropylcyclohexanone (5.0 g, 36 mmol) and benzylamine (3.54 mL, 32 mmol) in MeOH (40 mL) was added 4 Å molecular sieves (2 g). After 16 h at rt NaBH4 (2.45 g, 65 mmol) was added and the mixture stirred for a further 6 h. Water (3 mL) was added and the solvent was removed in vacuo. The residue was partitioned between NaHCO3 (150 mL) and EtOAc (150 mL), the aqueous layer was extracted with EtOAc (2×50 mL) and the combined organic phases were washed with brine (2×50 mL) and dried (MgSO4). Solvent was removed in vacuo and the residue purified by column chromatography (SiO2, NH4OH:MeOH:DCM 0.25:5:95) to give the product as a free base. 4M HCl in dioxane and Et2O were added to the residue, and the resulting precipitate was filtered to give the title compound: δH (CD3OD) 0.92-0.97 (6H, m), 1.17-1.26 (1H, m), 1.53-1.92 (9H, m), 3.21-3.29 (1H, m), 4.23 (2H, s) 7.44-7.54 (5H, m).

Workup

  1. customthe solvent was removed in vacuo
  2. customThe residue was partitioned between NaHCO3 (150 mL) and EtOAc (150 mL)
  3. extractionthe aqueous layer was extracted with EtOAc (2×50 mL)
  4. washthe combined organic phases were washed with brine (2×50 mL)
  5. dry with materialdried (MgSO4)
  6. customSolvent was removed in vacuo
  7. customthe residue purified by column chromatography (SiO2, NH4OH:MeOH:DCM 0.25:5:95)
  8. customto give the product as a free base
  9. filtrationthe resulting precipitate was filtered

Sources & evidence

ORD record
ord-425bfba4c3ef48809485547066a0966f
Source dataset
uspto-grants-2012_10
Patent number
US08278442B2

Reaction notes

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