HCID 68509056, compound → HCID 68512348, compound

HRID 1716589Notes

Reaction equation

HRID 1716589 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[CH2:13][CH:12]([CH2:17][N:18]1[CH2:23][CH2:22][CH:21]([N:24]3[C:28]4[CH:29]=[CH:30][C:31]([CH3:33])=[CH:32][C:27]=4[N:26]=[C:25]3[CH3:34])[CH:20]([CH2:35][OH:36])[CH2:19]1)[CH2:11]2)(C)(C)C>Cl.O1CCOCC1.C(Cl)Cl>[NH2:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[CH2:13][CH:12]([CH2:17][N:18]1[CH2:23][CH2:22][CH:21]([N:24]3[C:28]4[CH:29]=[CH:30][C:31]([CH3:33])=[CH:32][C:27]=4[N:26]=[C:25]3[CH3:34])[CH:20]([CH2:35][OH:36])[CH2:19]1)[CH2:11]2

Participants

5

Reactant 1

HCID 68509056HCID 68509056, compound

Product 1

HCID 68512348HCID 68512348, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

{2-[4-(2,5-Dimethyl-benzoimidazol-1-yl)-3-hydroxymethyl-piperidin-1-ylmethyl]-indan-5-yl}-carbamic acid tert-butyl ester (191 mg) was dissolved in 4M HCl in dioxane and stirred for 1 h after which all volatiles were removed under reduced pressure to yield a heavy oil which was suspended in CH2Cl2 and washed with 0.1 M NaOH. The organic phase was dried over Na2CO3. Filtration and removal of volatiles yielded [1-(5-amino-indan-2-ylmethyl)-4-(2,5-dimethyl-benzoimidazol-1-yl)-piperidin-3-yl]-methanol as a heavy oil (86 mg; 59%)

Workup

  1. customwere removed under reduced pressure
  2. customto yield a heavy oil which
  3. washwashed with 0.1 M NaOH
  4. dry with materialThe organic phase was dried over Na2CO3
  5. filtrationFiltration and removal of volatiles

Sources & evidence

ORD record
ord-621c1107af8c45fdb416e286d0564f1d
Source dataset
uspto-grants-2010_09
Patent number
US07803816B2

Reaction notes

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