Triethylamine → HCID 66930848, compound

HRID 1364137Notes

Reaction equation

HRID 1364137 reaction equation
Cl.Cl.[NH:3]([CH:5]1[CH2:10][CH2:9][N:8]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:7][CH2:6]1)[NH2:4].O=[C:19]1[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH2:21][CH:20]1[C:33](OCC)=[O:34].C(N(CC)CC)C>C(O)(C)(C)C>[O:34]=[C:33]1[CH:20]2[C:19]([CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH2:21]2)=[N:4][N:3]1[CH:5]1[CH2:10][CH2:9][N:8]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:7][CH2:6]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 44365701-tert-Butyl 4-ethyl 5-oxoazepane-1,4-dicarboxylateHCID 21193157Piperidine, 4-hydrazinyl-1-(phenylmethyl)-, hydrochloride (1:2)

Product 1

HCID 66930848HCID 66930848, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A mixture of 4-hydrazino-1-(phenylmethyl)piperidine dihydrochloride (commercially available from e.g. Aurora Screening Library) (2.68 g, 9.63 mmol) and tert-butanol (60 ml) was added to 1-(1,1-dimethylethyl) 4-ethyl 5-oxohexahydro-1H-azepine-1,4-dicarboxylate (may be prepared as described in Synthetic Communications (1992), 22(9), 1249-58) (2.50 g, 8.76 mmol) followed by triethylamine (7.33 ml, 52.59 mmol) and the resulting suspension warmed to reflux over ˜10 min under Argon. The resulting clear yellow solution was then kept at this temperature for 65 h. The mixture was then allowed to cool to room temperature over ˜2 h and the mixture reduced under vacuum to give a cream coloured solid residue. Purification by chromatography on silica gel eluting with dichloromethane:methanol 50:1→25:1→10:1 afforded a product which as partitioned between water and dichloromethane (100 ml each) the layers separated and the organic layer washed with more water (100 ml), followed by brine (100 ml) and then dried (Na2SO4), filtered and reduced to give the title compound (D47). MS (ES+) m/e 427 [M+H]+.

Workup

  1. temperaturethe resulting suspension warmed
  2. temperatureto reflux over ˜10 min under Argon
  3. customto give a cream
  4. customPurification by chromatography on silica gel eluting with dichloromethane:methanol 50:1→25:1→10:1
  5. customafforded a product which
  6. customas partitioned between water and dichloromethane (100 ml each) the layers
  7. customseparated
  8. washthe organic layer washed with more water (100 ml)
  9. dry with materialdried (Na2SO4)
  10. filtrationfiltered

Sources & evidence

ORD record
ord-5b10e7072b984ff582194fb512926721
Source dataset
uspto-grants-2011_02
Patent number
US07888347B2

Reaction notes

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