Hydrochloric Acid → HCID 14127930, compound

HRID 1073076Notes

Reaction equation

HRID 1073076 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH:4]([CH2:8][CH2:9][CH2:10][CH:11]2[CH2:16][CH2:15][CH:14]([NH2:17])[CH2:13][CH2:12]2)[CH2:3]1.Cl.[C:19]([C:23]1[CH:30]=[CH:29][C:26]([CH:27]=O)=[CH:25][CH:24]=1)([CH3:22])([CH3:21])[CH3:20].C([BH3-])#N.[Na+].C#N>CO>[C:19]([C:23]1[CH:24]=[CH:25][C:26]([CH2:27][NH:17][CH:14]2[CH2:13][CH2:12][CH:11]([CH2:10][CH2:9][CH2:8][CH:4]3[CH2:5][CH2:6][CH2:7][CH:2]([CH3:1])[CH2:3]3)[CH2:16][CH2:15]2)=[CH:29][CH:30]=1)([CH3:22])([CH3:20])[CH3:21]

Participants

7

Reactant 5

HCID 313Hydrochloric Acid2×HCID 768Hydrogen CyanideHCID 703244-tert-ButylbenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 14127929HCID 14127929, compound

Product 1

HCID 14127930HCID 14127930, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 11.9 g (0.05 mole) of 4-[3-(3-methylcyclohexyl)-propyl]cyclohexylamine in 50 ml of anhydrous methanol is acidified to pH 5-6 with a methanolic HCl solution, after which 8.1 g (0.05 mole) of 4-tert-butylbenzaldehyde and 15 g of dry molecular sieve (3 Å, Grace type 0564) are added and the mixture is cooled to 0° C. 1.6 g (0.025 mole) of sodium cyanoborohydride are added a little at a time to the stirred mixture, the latter is heated to room temperature and stirring is continued for 24 hours. Thereafter, the mixture is acidified with concentrated HCl, hydrogen cyanide formed is expelled by means of nitrogen, and the mixture is filtered and rendered alkaline with dilute NaOH. It is extracted several times with dichloromethane, the organic phase is dried over MgSO4 and evaporated down, and the residue is distilled to give 9.5 g (56% of theory) of a yellow oil of boiling point 236°- 242° C./0.4 mm (compound no. 65).

Workup

  1. temperaturethe latter is heated to room temperature
  2. customformed
  3. filtrationthe mixture is filtered
  4. extractionIt is extracted several times with dichloromethane
  5. dry with materialthe organic phase is dried over MgSO4
  6. customevaporated down
  7. distillationthe residue is distilled
  8. customto give 9.5 g (56% of theory) of a yellow oil of boiling point 236°- 242° C./0.4 mm (compound no

Sources & evidence

ORD record
ord-d911487a69bf4b1c8cc0a7e61909cd39
Source dataset
uspto-grants-1990_11
Patent number
US04968676

Reaction notes

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