alpha-Cyclohexylcyclohexanemethanamine → N,N-Dicyclohexylmethyl-N',N'-dibenzyl-2-butene-1,4-diamine

HRID 2255814Notes

Reaction equation

HRID 2255814 reaction equation
C(O[CH2:5][CH:6]=[CH:7][CH2:8][N:9]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=O)C.C1([CH:30]([NH2:37])[CH:31]2[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]2)CCCCC1>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:18]1([CH2:17][N:9]([CH2:10][CH:11]2[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]2)[CH2:8][CH:7]=[CH:6][CH2:5][N:37]([CH2:30][C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]1

Participants

5

Reactant 2

HCID 10774245alpha-CyclohexylcyclohexanemethanamineHCID 537897791-Acetoxy-4-dibenzylamino-2-butene

Product 1

HCID 57036974N,N-Dicyclohexylmethyl-N',N'-dibenzyl-2-butene-1,4-diamine

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-acetoxy-4-dibenzylamino-2-butene (10.1 g, 33 mmol) and dicyclohexylmethylamine (6.8 g, 32 mmol) in 50 ml of THF is treated with tetrakis(triphenylphosphine)palladium (0) (1.0 g, 0.9 mmol) and stirred at room temperature overnight. The reaction mixture is concentrated in vacuo to a solid which is redissolved in 100 ml of THF and treated with 25 ml of 20% aqueous sodium hydroxide. The mixture is stirred for one hour, concentrated and extracted with diethyl ether. The ether extracts are dried and concentrated to give a solid which is then purified by crystallization from isopropanol. The title compound is obtained in a yield of 9.7 g (65%) as a white solid melting at 61°-62° C.

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo to a solid which
  2. dissolutionis redissolved in 100 ml of THF
  3. additiontreated with 25 ml of 20% aqueous sodium hydroxide
  4. stirringThe mixture is stirred for one hour
  5. concentrationconcentrated
  6. extractionextracted with diethyl ether
  7. dry with materialThe ether extracts are dried
  8. concentrationconcentrated
  9. customto give a solid which
  10. customis then purified by crystallization from isopropanol

Sources & evidence

ORD record
ord-4a827efbcfb74871a0a9128d41411a4e
Source dataset
uspto-grants-1993_08
Patent number
US05240976

Reaction notes

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