1,4-Cyclohexanedimethanamine → HCID 178511242, compound

HRID 1986237Notes

Reaction equation

HRID 1986237 reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:8][CH2:7][CH:6]([CH2:9][NH2:10])[CH2:5][CH2:4]1.[S:11]1[C:15]([C:16]2[CH:21]=[CH:20][N:19]=[C:18](Cl)[N:17]=2)=[CH:14][C:13]2[CH:23]=[CH:24][CH:25]=[CH:26][C:12]1=2>C(O)(C)C.ClCCl>[NH2:1][CH2:2][C@@H:3]1[CH2:8][CH2:7][C@H:6]([CH2:9][NH:10][C:18]2[N:17]=[C:16]([C:15]3[S:11][C:12]4[CH:26]=[CH:25][CH:24]=[CH:23][C:13]=4[CH:14]=3)[CH:21]=[CH:20][N:19]=2)[CH2:5][CH2:4]1

Participants

5

Reactant 2

HCID 173541,4-CyclohexanedimethanamineHCID 147450254-(1-Benzothiophen-2-yl)-2-chloropyrimidine

Product 1

HCID 178511242HCID 178511242, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6344DichloromethaneSolvent

Procedure

4-Aminomethyl-cyclohexylmethyl-amine (cis/trans-mixture, ca. 2:1) (1.28 g, 9.00 mmol) is added to a stirred suspension of 4-benzo[b]thiophen-2-yl-2-chloro-pyrimidine (986 mg, 4.00 mmol) in isopropanol (13 mL) at ambient temperature under nitrogen. The resultant mixture is heated at 110° C. for 20 hours. At ambient temperature the mixture is diluted with dichloromethane (40 mL), washed with 1N NaOH (13 mL), and dried (MgSO4). After concentration and subsequent chromatographic purification on silica gel, eluting with 2 M NH3/MeOH in dichloromethane 0-20%, the title compound is obtained as a 2:1 cis/trans-mixture (1.24 g, 88% yield). ES+(m/z) 353 [M+H].

Workup

  1. washwashed with 1N NaOH (13 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationAfter concentration and subsequent chromatographic purification on silica gel
  4. washeluting with 2 M NH3/MeOH in dichloromethane 0-20%

Sources & evidence

ORD record
ord-a5316583bb2d43eaaa2f0bc851987d1a
Source dataset
uspto-grants-2009_06
Patent number
US07547691B2

Reaction notes

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