Acetic Acid → HCID 18617841, compound

HRID 1264320Notes

Reaction equation

HRID 1264320 reaction equation
[CH3:1][N:2]([CH3:17])[CH:3]1[CH2:8][CH2:7][N:6]([C:9]2[CH:16]=[CH:15]C(C#N)=[CH:11][CH:10]=2)[CH2:5][CH2:4]1.Cl.O.[C:20]([OH:23])(=[O:22])[CH3:21]>>[CH3:1][N:2]([CH3:17])[CH:3]1[CH2:4][CH2:5][N:6]([C:9]2[CH:16]=[CH:15][C:21]([C:20]([OH:23])=[O:22])=[CH:11][CH:10]=2)[CH2:7][CH2:8]1

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 962WaterHCID 18617570HCID 18617570, compound

Product 1

HCID 18617841HCID 18617841, compoundYield 85%

Procedure

280 mg (1.22 mmol) of 4-(4-dimethylamino-piperidin-1-yl)-benzonitrile (reference example 114a) was dissolved in 2 ml of acetic acid, 4 ml of 6 N HCl was added and the mixture stirred with reflux for 16 h. After cooling 20 ml of water was added and extracted with DCM (3×). The pH of the aqueous phase was adjusted to 5 with KOH pellets, white solid precipitated which was filtered off, washed and dried to give 257 mg of the title compound (85% yield). 1H NMR (CDCl3): δ 7.88 (dd, 2H), 6.98 (dd, 2H), 4.09 (d, 2H), 3.42 (m, 1H), 3.29 (t, 2H), 2.90 (s, 6H), 2.89-2.96 (m, 2H), 2.18 (m, 2H), 1.80 (dq, 2H). MS (ion spray) m/z 249 (M+H)+. 90% pure by analytical HPLC.

Workup

  1. temperaturewith reflux for 16 h
  2. additionwas added
  3. extractionextracted with DCM (3×)
  4. customprecipitated which
  5. filtrationwas filtered off
  6. washwashed
  7. customdried

Sources & evidence

ORD record
ord-38b704f9a26b42ae8295694fd99ef105
Source dataset
uspto-grants-2003_04
Patent number
US06541505B1

Reaction notes

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