tert-Butyl piperazine-1-carboxylate → HCID 68855483, compound

HRID 749677Notes

Reaction equation

HRID 749677 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH:12]3[CH2:13][CH2:14][CH2:15][CH2:16][CH:11]3[O:10][CH:9]2O)[CH:5]=[CH:6][CH:7]=1.[N:18]1(C(OC(C)(C)C)=O)[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C.C(Cl)Cl>[ClH:1].[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]([CH:12]2[CH2:13][CH2:14][CH2:15][CH2:16][CH:11]2[OH:10])[CH2:9][N:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 68855467HCID 68855467, compound

Product 1

HCID 68855483HCID 68855483, compoundYield 274.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 63651,1-DichloroethaneSolvent

Procedure

A solution of 3-(3-chlorophenyl)octahydro-1-benzofuran-2-ol (175 mg, 0.69 mmol) and tert-butyl 1-piperazinecarboxylate (128 mg, 0.69 mmol) in dichloroethane (3 mL) was treated with sodium trisacetoxyborohydride (220 mg, 1.04 mmol). The reaction was allowed to stir at room temperature for 16 h. The reaction was then diluted with methylene chloride and washed with a saturated aqueious solution of ammonium chloride (3 times). The organic layer was dried over magnesium sulfate and concentrated in vacuo and the product was purified via Biotage Horizon (FLASH 25 M, silica, gradient from 0% EtOAc/hexane to 30% EtOAc/hexane). This material was dissolved in methanol (0.5 mL) and treated with a saturated methanolic solution of hydrochloric acid (0.5 mL) followed by diethyl ether. After crystallizing in the refrigerator for 16 h, the resulting solid was collected, washed with diethyl ether and dried in vacuo to yield 250 mg (83%) 2-[1-(3-chlorophenyl)-2-piperazin-1-ylethyl]cyclohexanol dihydrochloride as a white solid. HRMS: calcd for C18H27ClN2O+H, 323.18901; found (ESI, [M+H]+), 323.1891.

Workup

  1. washwashed with a saturated aqueious solution of ammonium chloride (3 times)
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customthe product was purified via Biotage Horizon (FLASH 25 M, silica, gradient from 0% EtOAc/hexane to 30% EtOAc/hexane)
  5. dissolutionThis material was dissolved in methanol (0.5 mL)
  6. additiontreated with a saturated methanolic solution of hydrochloric acid (0.5 mL)
  7. customAfter crystallizing in the refrigerator for 16 h
  8. customthe resulting solid was collected
  9. washwashed with diethyl ether
  10. customdried in vacuo

Sources & evidence

ORD record
ord-0484734188ce4d70942dabc2ada8726c
Source dataset
uspto-grants-2008_07
Patent number
US07402698B2

Reaction notes

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