Tris(1,1-dimethylethyl)phosphine → HCID 69058421, compound

HRID 1453651Notes

Reaction equation

HRID 1453651 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][CH:20]=1)[CH2:5][N:6]1[C:12](=[O:13])[CH2:11][CH2:10][CH2:9][C:8]2[CH:14]=[CH:15][CH:16]=[CH:17][C:7]1=2.CC(C)([O-])C.[Na+].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.[C:40]([O:44][C:45]([N:47]1[CH2:52][CH2:51][NH:50][CH2:49][CH2:48]1)=[O:46])([CH3:43])([CH3:42])[CH3:41]>C1(C)C(C)=CC=CC=1.C(OCC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:40]([O:44][C:45]([N:47]1[CH2:52][CH2:51][N:50]([C:2]2[CH:20]=[CH:19][CH:18]=[C:4]([CH2:5][N:6]3[C:12](=[O:13])[CH2:11][CH2:10][CH2:9][C:8]4[CH:14]=[CH:15][CH:16]=[CH:17][C:7]3=4)[CH:3]=2)[CH2:49][CH2:48]1)=[O:46])([CH3:43])([CH3:41])[CH3:42]

Participants

8

Reactant 4

HCID 83681Tris(1,1-dimethylethyl)phosphineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 22324258HCID 22324258, compoundHCID 23676156Sodium t-butoxide

Product 1

HCID 69058421HCID 69058421, compoundYield 97.3%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 3283Diethyl EtherSolventHCID 7237O-XyleneSolvent

Procedure

A mixture of 0.5 g (1.51 mmole) 1-(3-bromo-benzyl)-1,3,4,5-tetrahydro-benzo[b]azepin-2-one, 0.203 g sodium tert-butoxide, 0.04 g (0.16 mmole) tri-tert-butyl phosphine, 0.04 g (0.16 mmole) palladium(II)acetate, and 0.3 g piperazin-1-yl carboxylic acid tert-butyl ester in 5 mL xylene was heated at 105° under N2 for 1.5 hrs. The mixture was diluted with 5 mL ethyl ether and then filtered through a pad of 10 g silica gel 230-400 mesh. 4-[3-(2-Oxo-2,3,4,5-tetrahydro-benzo[b]azepin-1-ylmethyl)-phenyl]-piperazine-1-carboxylic acid tert-butyl ester was eluted with 20% ethyl acetate/hexane to yield 0.64 g of a heavy syrup. M+H=436.

Workup

  1. temperaturewas heated at 105° under N2 for 1.5 hrs
  2. filtrationfiltered through a pad of 10 g silica gel 230-400 mesh
  3. wash4-[3-(2-Oxo-2,3,4,5-tetrahydro-benzo[b]azepin-1-ylmethyl)-phenyl]-piperazine-1-carboxylic acid tert-butyl ester was eluted with 20% ethyl acetate/hexane

Sources & evidence

ORD record
ord-0b4183f0a8de47a19b7a15fd6c782b7f
Source dataset
uspto-grants-2009_01
Patent number
US07476675B2

Reaction notes

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