HCID 23500659, compound → HCID 23500726, compound

HRID 1835857Notes

Reaction equation

HRID 1835857 reaction equation
Cl.C(N1CCCC2(C3C(=CC=CC=3)CN2)C1=O)CC.Cl.[CH2:21]([N:24]1[CH2:29][CH2:28][CH2:27][C:26]2([C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[C:31](=[O:38])[NH:30]2)[CH2:25]1)[CH2:22][CH3:23]>>[CH2:21]([N:24]1[CH2:29][CH:28]=[CH:27][C:26]2([C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[C:31](=[O:38])[NH:30]2)[CH2:25]1)[CH2:22][CH3:23]

Participants

3

Reactant 2

HCID 23500659HCID 23500659, compoundHCID 69913891HCID 69913891, compound

Product 1

HCID 23500726HCID 23500726, compoundYield 14.6%

Procedure

1′-Propylspiro[isoindoline-3,3′-piperidin]-one hydrochloride. The compound from STEP B (6.60 g) was cyclised according to the general Heck procedure described in EXAMPLE 1 to give an oil which was chromatographed on silica gel with ethyl acetate/n-heptane as the eluent to give 830 mg 1′-propylspiro-[isoindoline-3,3′-1,2,3,6-tetrahydropyridin]-1-one as an oil. This compound was hydrogenated as described in EXAMPLE 1 yielding the free base of the title compound as white crystals. The title compound was also prepared from cyclization of the STEP C compound followed by hydrogenation-debenzylation plus propylation. 13C NMR (CDCl3): δ 169.44, 150.10, 131.77, 131.58, 128.51, 124.14, 121.56, 62.74, 60.87, 60.26, 53.24, 34.88, 23.34, 19.00. 11.82; MS(TSP+) m/z: 245 (M+H+, 100); MS(CI, NH3): 245 (M+H+, 100), 180 (3). MP: 110-112°.

Workup

  1. customto give an oil which
  2. customwas chromatographed on silica gel with ethyl acetate/n-heptane as the eluent

Sources & evidence

ORD record
ord-6afe2a8dfa3647d887a5eacc52baa6ec
Source dataset
uspto-grants-2004_08
Patent number
US06774132B1

Reaction notes

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