N,N,N',N'-Tetramethylethylenediamine → HCID 178448037, compound

HRID 375781Notes

Reaction equation

HRID 375781 reaction equation
[Li]CCCC.[CH2:6]([C@H:9]1[CH2:14][CH2:13][C@H:12]([C@H:15]2[CH2:20][CH2:19][C@H:18]([CH2:21][CH2:22][C:23]3[CH:28]=[C:27]([F:29])[CH:26]=[C:25]([F:30])[CH:24]=3)[CH2:17][CH2:16]2)[CH2:11][CH2:10]1)[CH2:7][CH3:8].CN(CCN(C)C)C.[Cl:39]N1C(=O)CCC1=O>C1COCC1.C(OCC)C.O>[CH2:6]([C@H:9]1[CH2:14][CH2:13][C@H:12]([C@H:15]2[CH2:20][CH2:19][C@H:18]([CH2:21][CH2:22][C:23]3[CH:24]=[C:25]([F:30])[C:26]([Cl:39])=[C:27]([F:29])[CH:28]=3)[CH2:17][CH2:16]2)[CH2:11][CH2:10]1)[CH2:7][CH3:8]

Participants

8

Reactant 4

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 31398ChlorosuccinimideHCID 178418339ButyllithiumHCID 178448036HCID 178448036, compound

Product 1

HCID 178448037HCID 178448037, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

0.1 mol of n-BuLi (1.5M in hexane) is added dropwise at about -65° to a solution of 0.1 mol of 1-[trans-4-(trans-4-n-propylcyclohexyl)cyclohexyl]-2-(3,5-difluorophenyl)ethane (prepared according to scheme 3) and 0.1 mol of TMEDA in 300 ml of THF. Stirring at this temperature is continued for another 30 minutes, and 0.2 mol of N-chlorosuccinimide in 70 ml of THF are then slowly added. After the addition is completed, the mixture is allowed to warm to -20° and hydrolyzed with H2O. Diethyl ether is added until the product is completely dissolved. Extractive work-up and purification by chromatography and crystallization gives 1-[trans-4-(trans-4-n-propylcyclohexyl)cyclohexyl]-2-(4-chloro-3,5-difluorophenyl)ethane, C 88 N 129 I.

Workup

  1. additionAfter the addition
  2. dissolutionis completely dissolved
  3. customExtractive work-up and purification
  4. customby chromatography and crystallization

Sources & evidence

ORD record
ord-307d073af8c9451ba28becbb763c60a1
Source dataset
uspto-grants-1996_01
Patent number
US05487845

Reaction notes

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