Sodium Cyanide → HCID 58188951, compound

HRID 1423149Notes

Reaction equation

HRID 1423149 reaction equation
[CH2:1]([C@H:8]1[CH2:13][N:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[CH:15]=2)[CH2:11][CH2:10][N:9]1[C:28]([C:30]1([C:33]([O:35]C)=O)[CH2:32][CH2:31]1)=[O:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C-]#[N:38].[Na+]>N.CO>[CH2:1]([C@H:8]1[CH2:13][N:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH:23]3[CH2:24][CH2:25][CH2:26][CH2:27]3)[CH:15]=2)[CH2:11][CH2:10][N:9]1[C:28]([C:30]1([C:33]([NH2:38])=[O:35])[CH2:31][CH2:32]1)=[O:29])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 66826509HCID 66826509, compound

Product 1

HCID 58188951HCID 58188951, compoundYield 22%

Reagents, catalysts & solvents 2

HCID 222AmmoniaSolventHCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

A solution of (S)-methyl 1-(2-benzyl-4-(3-(cyclopentyloxy)-4-methoxyphenyl)piperazine-1-carbonyl)cyclopropanecarboxylate (123 mg, 0.25 mmol) was dissolved in a 7 N ammonia solution in MeOH (10 mL), treated with catalytic amount of sodium cyanide, then heated in a sealed tube at 80° C. for 5 days. The reaction mixture was then evaporated, washed with water and air dried to afford a residue then purified by silica gel flash chromatography with 50% then 100% EtOAc/hexanes as eluant to afford the title compound as colorless foam (26 mg, 22%). LC/MS (Method B) 3.49 min, [M+1]+ 478.

Workup

  1. customThe reaction mixture was then evaporated
  2. washwashed with water and air
  3. customdried
  4. customto afford a residue
  5. customthen purified by silica gel flash chromatography with 50%

Sources & evidence

ORD record
ord-ece6bcc696c64b6695fe069fe1257810
Source dataset
uspto-grants-2015_01
Patent number
US08927546B2

Reaction notes

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