Triethylamine → HCID 178453934, compound

HRID 645463Notes

Reaction equation

HRID 645463 reaction equation
Cl.[CH2:2]1[C:10]2[C:5](=[C:6]([N:11]3[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)[CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3]1.[C:17]([O:21][C:22](=[O:32])[NH:23][C@H:24]1[CH2:29][CH2:28][C@H:27]([CH:30]=O)[CH2:26][CH2:25]1)([CH3:20])([CH3:19])[CH3:18].C(N(CC)CC)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])[O-].[K+].[K+]>ClC(Cl)C.O>[C:17]([O:21][C:22](=[O:32])[NH:23][C@H:24]1[CH2:25][CH2:26][C@H:27]([CH2:30][N:14]2[CH2:13][CH2:12][N:11]([C:6]3[CH:7]=[CH:8][CH:9]=[C:10]4[C:5]=3[CH2:4][CH2:3][CH2:2]4)[CH2:16][CH2:15]2)[CH2:28][CH2:29]1)([CH3:20])([CH3:18])[CH3:19]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 210731941-Indan-4-yl-piperazine hydrochlorideHCID 178453955HCID 178453955, compound

Product 1

HCID 178453934HCID 178453934, compoundYield 82.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 63651,1-DichloroethaneSolvent

Procedure

3.58 g (15 mmol) of 1-(indan-4-yl)-piperazine hydrochloride and 3.41 g (15 mmol) of trans-(4-formyl-cyclohexyl)-carbamic acid tert-butylester were dissolved in dichloroethane (120 ml), 2.1 ml (15 mmol) triethylamine was added, then 4.6 g (22 mmol) sodium triacetoxyborohydride was added portionswise and the reaction mixture was stirred for 20 hours at ambient temperature, then 20% potassium carbonate solution in water (40 ml) was added. The organic layer was separated, dried and evaporated to dryness in vacuo. The precipitate was recrystallized from acetonitrile to give the title compound 5.1 g (yield: 82.2%), m.p.: 131-4° C.

Workup

  1. customThe organic layer was separated
  2. customdried
  3. customevaporated to dryness in vacuo
  4. customThe precipitate was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-03a98b59572c4e0b93557da14c3f2dd7
Source dataset
uspto-grants-2010_04
Patent number
US07705003B2

Reaction notes

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