Quinuclidine, 3-amino-, dihydrochloride → HCID 18381563, compound

HRID 2298069Notes

Reaction equation

HRID 2298069 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:19]([CH:22]=O)=[CH:18][C:3]=1[C:4]([NH:6][CH2:7][C:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2)=[O:5].Cl.Cl.[N:26]12[CH2:33][CH2:32][CH:29]([CH2:30][CH2:31]1)[CH:28]([NH2:34])[CH2:27]2.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[N:26]12[CH2:33][CH2:32][CH:29]([CH2:30][CH2:31]1)[CH:28]([NH:34][CH2:22][C:19]1[CH:20]=[CH:21][C:2]([Cl:1])=[C:3]([CH:18]=1)[C:4]([NH:6][CH2:7][C:8]13[CH2:17][CH:12]4[CH2:11][CH:10]([CH2:16][CH:14]([CH2:13]4)[CH2:15]1)[CH2:9]3)=[O:5])[CH2:27]2

Participants

5

Reactant 3

HCID 197853Quinuclidine, 3-amino-, dihydrochlorideHCID 5049666Sodium triacetoxyborohydrideHCID 120853462-Chloro-5-formyl-N-(tricyclo [3.3.1.13,7]dec-1-ylmethyl)-benzamide

Product 1

HCID 18381563HCID 18381563, compoundYield 3.3%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Prepared according to the method described in Example 31b from 2-chloro-5-formyl-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide (0.30 g, Example 31a), 1-azabicyclo[2.2.2]octan-3-amine dihydrochloride salt (0.18 g), sodium triacetoxyborohydride (0.135 g) and 1,2-dichloroethane (10 ml). The residue was purified by chromatography over silica gel eluting with ethyl acetate: iso-hexane (1:1) followed by ethyl acetate: ethanol (95:5). Repurification by chromatography over silica gel eluting with dichloromethane: methanol (95:5) then (9:1) gave the title compound as a white gum (0.013 g).

Workup

  1. customPrepared
  2. customThe residue was purified by chromatography over silica gel eluting with ethyl acetate: iso-hexane (1:1)
  3. customRepurification by chromatography over silica gel eluting with dichloromethane: methanol (95:5)

Sources & evidence

ORD record
ord-4b6b6cd578e04fb89f0b2b57ecc02fcc
Source dataset
uspto-grants-2002_12
Patent number
US06492355B1

Reaction notes

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