Hydrochloric Acid → HCID 21193444, compound

HRID 443308Notes

Reaction equation

HRID 443308 reaction equation
[C:1]1([N:7]2[CH2:12][CH2:11][CH:10]([NH2:13])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:14]([C:16]1[CH:31]=[CH:30][C:19]([CH2:20][N:21]2[C:25](CC([O-])=O)=[CH:24][N:23]=[CH:22]2)=[CH:18][CH:17]=1)#[N:15].[Li+].[OH2:33].ON1C2C=CC=[CH:43][C:38]=2N=N1.[ClH:44].CN(C)CCCN=C=NCC.C(N(CC)C(C)C)(C)C.Cl>C(#N)C>[ClH:44].[C:14]([C:16]1[CH:17]=[CH:18][C:19]([CH2:20][N:21]2[CH:25]=[CH:24][N:23]([CH2:38][C:43]([NH:13][CH:10]3[CH2:9][CH2:8][N:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[CH2:12][CH2:11]3)=[O:33])[CH2:22]2)=[CH:30][CH:31]=1)#[N:15]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 211933471-Phenylpiperidin-4-amineHCID 67586058HCID 67586058, compound

Product 1

HCID 21193444HCID 21193444, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-Phenylpiperidin-4-ylamine (40 mg, 0.227 mmol), lithium [3-(4-cyanobenzyl)-3H-imidazol-4-yl]acetate (56 mg, 0.227 mmol), 1-hydroxybenzotriazole hydrate (46 mg, 0.34 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (87 mg, 0.45 mmol), and N,N-diisopropylethylamine (99 μL, 0.57 mmol) were added to degassed DMF (2 mL) and the mixture was stirred for 18 hrs at room temperature then concentrated in vacuo. The residue was added to sat. NaHCO3 (aq) (5 mL) and extracted with dichloromethane (3×3 mL). The combined organic extracts were dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was chromatographed on silica gel, eluting with dichloromethane--5% methanol--0.05% NH4OH to give the product as a free base. This was lyophilized from HCl (aq)--acetonitrile to give the title compound as a white solid.

Workup

  1. customto degassed DMF (2 mL)
  2. concentrationthen concentrated in vacuo
  3. additionThe residue was added to sat. NaHCO3 (aq) (5 mL)
  4. extractionextracted with dichloromethane (3×3 mL)
  5. dry with materialThe combined organic extracts were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was chromatographed on silica gel
  9. washeluting with dichloromethane--5% methanol--0.05% NH4OH
  10. customto give the product as a free base

Sources & evidence

ORD record
ord-5022f6e277a24a478efe83ac038d4d31
Source dataset
uspto-grants-1999_04
Patent number
US05891889

Reaction notes

Loading…