Triethylamine → HCID 178453908, compound

HRID 645462Notes

Reaction equation

HRID 645462 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:33])[NH:23][C@H:24]1[CH2:29][CH2:28][C@H:27]([CH2:30][CH:31]=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:33])[NH:23][C@H:24]1[CH2:25][CH2:26][C@H:27]([CH2:30][CH2:31][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])([CH3:19])[CH3:18]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 210731941-Indan-4-yl-piperazine hydrochlorideHCID 178453924HCID 178453924, compound

Product 1

HCID 178453908HCID 178453908, compoundYield 85.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 63651,1-DichloroethaneSolvent

Procedure

3.58 g (15 mmol) of 1-(indan-4-yl)-piperazine hydrochloride and 3.62 g (15 mmol) of trans-4-(2-oxoethyl)cyclohexyl-carbamic acid tert-butyl ester 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 5.5 g (yield: 85.8%), m.p.: 115-8° 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-ad46cd87e58e41deb98dd2372c7fa4f6
Source dataset
uspto-grants-2010_04
Patent number
US07705003B2

Reaction notes

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