1,4'-Bipiperidine → HCID 66905434, compound

HRID 2041011Notes

Reaction equation

HRID 2041011 reaction equation
S=[C:2]1[NH:6][C:5]2[CH:7]=[C:8]([C:11]([O:13][CH3:14])=[O:12])[CH:9]=[CH:10][C:4]=2[O:3]1.[N:15]1([CH:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1>C1(C)C(C)=CC=CC=1.ClCCl>[N:15]1([CH:21]2[CH2:26][CH2:25][N:24]([C:2]3[O:3][C:4]4[CH:10]=[CH:9][C:8]([C:11]([O:13][CH3:14])=[O:12])=[CH:7][C:5]=4[N:6]=3)[CH2:23][CH2:22]2)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

5

Reactant 2

HCID 786071,4'-BipiperidineHCID 53069482-Mercapto-1,3-benzoxazole-5-carboxylic acid methyl ester

Product 1

HCID 66905434HCID 66905434, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7237O-XyleneSolvent

Conditions

Temperature
130 °C

Procedure

Methyl 2-thioxo-2,3-dihydrobenzo[d]oxazole-5-carboxylate (Example 94A, 300 mg, 1.43 mmol) and 1,4′-bipiperidine (483 mg, 2.87 mmol) were combined in xylene (2 mL). The mixture was heated in a microwave to 130° C. for 20 minutes. The reaction mixture was diluted with dichloromethane, washed with water, and the organic layer was absorbed on silica gel. The crude mixture was purified using silica gel chromatography (40 g column) eluting with a gradient of methanol/dichloromethane (3-18%) to afford the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 1.38-1.50 (m, 2 H) 1.54-1.72 (m, 5 H) 1.95 (d, J=12.89 Hz, 2 H) 2.46-2.59 (m, 6 H) 3.03-3.16 (m, 2 H) 3.91 (s, 3 H) 4.32-4.36 (m, 1 H) 4.36-4.41 (m, 1 H) 7.25 (d, 1 H) 7.79 (dd, J=8.48, 1.70 Hz, 1 H) 8.00 (d, J=1.70 Hz, 1 H); MS (ESI+) m/z 344.3 (M+H)+.

Workup

  1. washwashed with water
  2. customthe organic layer was absorbed on silica gel
  3. customThe crude mixture was purified
  4. washeluting with a gradient of methanol/dichloromethane (3-18%)

Sources & evidence

ORD record
ord-123b0dabf85944fcb22a0be57981722c
Source dataset
uspto-grants-2013_11
Patent number
US08580968B2

Reaction notes

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