HCID 9797645, compound → HCID 9819036, compound

HRID 861381Notes

Reaction equation

HRID 861381 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][C:10]2[CH2:11][CH2:12][N:13]([CH2:16][C:17]3[NH:18][C:19]4[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=4[N:21]=3)[CH2:14][CH:15]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(OCC)(=O)C.O.[Pt](=O)=O>[C:1]1([CH2:7][CH2:8][CH2:9][CH:10]2[CH2:11][CH2:12][N:13]([CH2:16][C:17]3[NH:21][C:20]4[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=4[N:18]=3)[CH2:14][CH2:15]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 9797645HCID 9797645, compound

Product 1

HCID 9819036HCID 9819036, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 11139377Platinum dioxide monohydrateCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-(4-[3-phenylpropyl]-1,2,3,6-tetrahydropyridin-1-ylmethyl)benzimidazole (1.01 g, 3.05 mmol) and platinum (IV) oxide hydrate (56 mg) in ethyl acetate (75 ml) was hydrogenated on a Parr apparatus (30 psi maximum) for 70 minutes. Fresh catalyst was added (40 mg) and the mixture hydrogenated for a further 2.5 h. The mixture was filtered and evaporated to dryness. Flash chromatography eluting with 7.5% methanol in dichloromethane followed by recrystallisation from ethyl acetate/petrol (60°-80° C.) gave the title compound (0.52 g, 52%) as a white solid, m.p. 140°-141° C.; (Found: C, 79.25; H, 8.07; N, 12.39. C22H27N3 requires C, 79.24; H, 8.16; N, 12.60%); δH (DMSO-d6) 1.19 (SH, m, 2×CH2 +piperidinyl CH), 1.57 (4H, m, 2×CH2), 2.02 (2H, m, CH2), 2.55 (2H, m, piperidinyl CH2), 2.81 (2H, m, piperidinyl CH2), 3.66 (2H, s, CH2N), 7.15 (SH, m, ArH), 7.26 (2H, m, ArH), 7.43 (1H, br d, ArH), 7.51 (1H, br d, ArH), and 12.16 (1H, br s, N3H); m/z (CI+, NH3) 334 (M+1)+.

Workup

  1. additionFresh catalyst was added (40 mg)
  2. waitthe mixture hydrogenated for a further 2.5 h
  3. filtrationThe mixture was filtered
  4. customevaporated to dryness
  5. washFlash chromatography eluting with 7.5% methanol in dichloromethane
  6. customfollowed by recrystallisation from ethyl acetate/petrol (60°-80° C.)

Sources & evidence

ORD record
ord-e3f120136ca74f1785682ef071fee4e8
Source dataset
uspto-grants-1998_02
Patent number
US05714498

Reaction notes

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