Hydrochloric Acid → HCID 18624253, compound

HRID 1860627Notes

Reaction equation

HRID 1860627 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([C:9]2([C:19]#[N:20])[CH:16]3[CH2:17][CH:12]4[CH2:13][CH:14]([CH2:18][CH:10]2[CH2:11]4)[CH2:15]3)[CH:6]=[CH:7][CH:8]=1)[CH3:2].[ClH:21]>C1COCC1>[ClH:21].[CH2:1]([C:3]1[CH:4]=[C:5]([C:9]2([CH2:19][NH2:20])[CH:10]3[CH2:18][CH:14]4[CH2:13][CH:12]([CH2:17][CH:16]2[CH2:15]4)[CH2:11]3)[CH:6]=[CH:7][CH:8]=1)[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 18624266HCID 18624266, compound

Product 1

HCID 18624253HCID 18624253, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-(3-ethylphenyl)-2-adamantanecarbonitrile (265 mg, 1 mmol) in dry THF (5 mL) under argon was treated with 1-M BH3 in THF (3.3 mL, 3.3 mmol), refluxed for 2 h, cooled to room temperature, treated with 6-M HCl (10 mL), refluxed for 0.25 h, cooled to room temperature and extracted with CHCl3 (2×10 mL). The combined extracts were washed with water (2×5 mL), dried (MgSO4), concentrated in vacuo and purified by chromatography [SiO2; EtOAc-MeOH (9:1)] to give the title compound (258 mg, 85%) as a white solid: mp 89-90° C.; IR νmax (Nujol)/cm−1 3395, 2922, 1603, 1489, 1458, 1376, 1100, 797, 734 and 713; NMR δH (400 MHz, DMSO-d6) 1.19 (3H, d, J 7.5 Hz), 1.41-1.57 (2H, m), 1.60-1.75 (6H, m), 1.89 (1H, s), 2.06-2.15 (2H, m), 2.46-2.64 (5H, m), 3.05 (2H, s) and 7.02-7.33 (7H, m); Anal. Calcd for C19H28ClN.0.2 H2O: C, 73.74; H, 9.25; N, 4.53. Found: C, 73.90; H, 9.28; N, 4.53.

Workup

  1. temperaturerefluxed for 2 h
  2. temperaturerefluxed for 0.25 h
  3. temperaturecooled to room temperature
  4. extractionextracted with CHCl3 (2×10 mL)
  5. washThe combined extracts were washed with water (2×5 mL)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. custompurified by chromatography [SiO2; EtOAc-MeOH (9:1)]

Sources & evidence

ORD record
ord-468d9808fecf4842abe4389810fe55a1
Source dataset
uspto-grants-2003_03
Patent number
US06531511B1

Reaction notes

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