Ammonium Chloride → HCID 44252105, compound

HRID 2063715Notes

Reaction equation

HRID 2063715 reaction equation
[CH2:1]([Mg]Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:10][N:11]([CH3:27])[C:12]1([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=2)[CH2:17][CH2:16][CH:15]([CH:18]=[O:19])[CH2:14][CH2:13]1.[Cl-].[NH4+]>O1CCCC1>[CH3:10][N:11]([CH3:27])[C:12]1([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=2)[CH2:17][CH2:16][CH:15]([CH:18]([OH:19])[CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 866346814-Dimethylamino-4-(3-fluorophenyl)cyclohexanecarbaldehydeHCID 178418336HCID 178418336, compound

Product 1

HCID 44252105HCID 44252105, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 2 M solution of benzylmagnesium chloride in tetrahydrofuran (6.00 ml, 12 mmol) was added dropwise to a solution of 4-dimethylamino-4-(3-fluorophenyl)cyclohexanecarbaldehyde (1.49 g, 5.97 mmol) in anhydrous tetrahydrofuran (30 ml), while cooling with ice. The mixture was stirred at room temperature for 2 d and saturated ammonium chloride solution (30 ml) was then added, while cooling with ice. The tetrahydrofuran was removed i. vac. and the residue was brought to pH 8 with 4 M sodium hydroxide solution. The aqueous suspension was extracted with diethyl ether (3×30 ml). The combined organic phases were dried with sodium sulfate and concentrated i. vac. The crude product (2.18 g) was purified by flash chromatography with methylene chloride/methanol [95:5+1% NH3 (32% in H2O)]. The impure polar diastereoisomer (500 mg) was purified again by flash chromatography with methylene chloride/methanol [95:5+1% NH3 (32% in H2O)].

Workup

  1. temperaturewhile cooling with ice
  2. temperaturewhile cooling with ice
  3. customThe tetrahydrofuran was removed i
  4. extractionThe aqueous suspension was extracted with diethyl ether (3×30 ml)
  5. dry with materialThe combined organic phases were dried with sodium sulfate
  6. concentrationconcentrated i
  7. customThe crude product (2.18 g) was purified by flash chromatography with methylene chloride/methanol [95:5+1% NH3 (32% in H2O)]
  8. customThe impure polar diastereoisomer (500 mg) was purified again by flash chromatography with methylene chloride/methanol [95:5+1% NH3 (32% in H2O)]

Sources & evidence

ORD record
ord-619b3a3f13004efeb27e418bec6e7154
Source dataset
uspto-grants-2012_10
Patent number
US08288406B2

Reaction notes

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