Acetic Acid → N-Cyclopropylcyclohexanamine

HRID 475692Notes

Reaction equation

HRID 475692 reaction equation
[C:1]1(=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:8]1([NH2:11])[CH2:10][CH2:9]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].CC(O)=O.Cl>ClC(Cl)C.O>[CH:8]1([NH:11][CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[CH2:10][CH2:9]1

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 7967CyclohexanoneHCID 69828CyclopropylamineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 20114456N-Cyclopropylcyclohexanamine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 63651,1-DichloroethaneSolvent

Procedure

To cyclohexanone (1.0 mL, 10 mmol) in dichloroethane (30 mL) was added cyclopropylamine (0.70 mL, 10 mmol), NaBH(OAc)3 (3.18 g, 15 mmol) and AcOH (0.57 mL, 10 mmol). The reaction was stirred at room temperature for 10 h. The reaction mixture was poured into water (60 mL) and acidified to pH 2 with 5 N HCl followed by removal of the organic portion. The aqueous portion was brought to pH>12 with 5 N NaOH and extracted with CH2Cl2 (3×30 mL). The collected organic extracts were dried with Na2SO4 and the volatile organics were removed in vacuo to afford the desired intermediate.

Workup

  1. customfollowed by removal of the organic portion
  2. extractionextracted with CH2Cl2 (3×30 mL)
  3. dry with materialThe collected organic extracts were dried with Na2SO4
  4. customthe volatile organics were removed in vacuo

Sources & evidence

ORD record
ord-96b9fa93e03f4ce4bafc8366aa31db51
Source dataset
uspto-grants-2014_01
Patent number
US08637576B2

Reaction notes

Loading…