Aluminium lithium hydride → HCID 178463898, compound

HRID 896644Notes

Reaction equation

HRID 896644 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:13][CH2:12][C@H:11]([N:14]([CH2:18][CH2:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:15](=O)[CH3:16])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1.CCOCC>[CH2:15]([N:14]([C@H:11]1[CH2:10][CH2:9][C@H:8]([C:5]2[CH:6]=[CH:7][C:2]([OH:1])=[CH:3][CH:4]=2)[CH2:13][CH2:12]1)[CH2:18][CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH3:16]

Participants

5

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 178474714HCID 178474714, compound

Product 1

HCID 178463898HCID 178463898, compoundYield 48.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of trans-N-[4-(4-hydroxyphenyl)cyclohexyl]-N-(3-phenylpropyl)acetamide (282 mg, 0.80 mmol) in anhydrous THF (5 mL) was added LiAlH4 (1.2 mL of a 1M solution in Et2O, 1.2 mmol). After 18 hours, the reaction was quenched by addition of a mixture of H2O (2 mL), 2N NaOH (4 mL), and saturated NaCl (2 mL). The resulting mixture was diluted with Et2O (100 mL) and the resulting mixture was filtered. The filtrate was dried (Na2SO4) and concentrated under reduced pressure. Purification by flash chromatography (90:9:1 CH2Cl2:MeOH:NH4OH) gave trans-4-{4-[N-ethyl-N-(3-phenylpropyl)-amino]cyclohexyl}phenol (130 mg, 48%) as a white solid: mp 192-194° C.; IR (KBr): 3197, 2939, 1614, 1516 cm−1; 1H NMR (500 MHz, DMSO-d6) δ 9.16 (br s, 1H), 7.35-7.23 (m, 5H), 7.02 (d, J=8 Hz, 2H), 6.70 (d, J=8 Hz, 2H), 3.35-3.12 (m, 5H), 2.68 (q, J=5, 2 Hz, 2H), 2.42 (tt, J=9, 2 Hz, 1H), 2.12 (br d, J=9 Hz, 2H), 2.10 (m, 2H), 1.87 (br d, J=9 Hz, 2H), 1.63 (dddd, J=9, 9, 9, 2 Hz, 2H), 1.53 (dddd, J=9, 9, 9, 2 Hz, 2H), 1.27 (t, J=5 Hz, 3H); CI-MS (methane) (m/z): 338 [M+H]+; HPLC: method A, 8.80 minutes (97.8%); method B, 10.66 minutes (99.9%); Anal. Calcd for C23H31NO.HCl.0.125H2O: C, 73.43; H, 8.64; N, 3.72. Found: C, 73.36; H, 8.75; N, 3.56.

Workup

  1. customthe reaction was quenched by addition of a mixture of H2O (2 mL), 2N NaOH (4 mL), and saturated NaCl (2 mL)
  2. additionThe resulting mixture was diluted with Et2O (100 mL)
  3. filtrationthe resulting mixture was filtered
  4. dry with materialThe filtrate was dried (Na2SO4)
  5. concentrationconcentrated under reduced pressure
  6. customPurification by flash chromatography (90:9:1 CH2Cl2:MeOH:NH4OH)

Sources & evidence

ORD record
ord-98c701c02e7542f69e0eb864ad4d15f8
Source dataset
uspto-grants-2005_07
Patent number
US06919377B2

Reaction notes

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