Triphenylphosphine → 2-Cyclopropylmethyl-9-(1-isopropyl-piperidin-4-yloxy)-2,3,4,5-tetrahydro-[1,4]diazepino[1,2-a]indol-1-one

HRID 2105417Notes

Reaction equation

HRID 2105417 reaction equation
[CH:1]1([CH2:4][N:5]2[CH2:19][CH2:18][CH2:17][N:8]3[C:9]4[CH:10]=[CH:11][C:12]([OH:16])=[CH:13][C:14]=4[CH:15]=[C:7]3[C:6]2=[O:20])[CH2:3][CH2:2]1.[CH:21]([N:24]1[CH2:29][CH2:28][CH:27](O)[CH2:26][CH2:25]1)([CH3:23])[CH3:22].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)(C)C)=O)=O)(C)C>>[CH:1]1([CH2:4][N:5]2[CH2:19][CH2:18][CH2:17][N:8]3[C:9]4[CH:10]=[CH:11][C:12]([O:16][CH:27]5[CH2:28][CH2:29][N:24]([CH:21]([CH3:23])[CH3:22])[CH2:25][CH2:26]5)=[CH:13][C:14]=4[CH:15]=[C:7]3[C:6]2=[O:20])[CH2:2][CH2:3]1

Participants

5

Reactant 4

HCID 11776TriphenylphosphineHCID 796811-Isopropylpiperidin-4-olHCID 6034084Di-tert-butyl diazene-1,2-dicarboxylateHCID 684610882-Cyclopropylmethyl-9-hydroxy-2,3,4,5-tetrahydro-[1,4]diazepino[1,2-a]indol-1-one

Product 1

HCID 529480082-Cyclopropylmethyl-9-(1-isopropyl-piperidin-4-yloxy)-2,3,4,5-tetrahydro-[1,4]diazepino[1,2-a]indol-1-oneYield 45%

Procedure

The title compound was synthesized in analogy to example 1, from 2-cyclopropylmethyl-9-hydroxy-2,3,4,5-tetrahydro-[1,4]diazepino[1,2-a]indol-1-one, 1-isopropyl-piperidin-4-ol (commercially available), triphenylphosphine and di-tert-butylazodicarboxylate, to give the desired product as a light yellow solid (45%).

Sources & evidence

ORD record
ord-967e641e05b2414aa2c2447497f0cf07
Source dataset
uspto-grants-2009_08
Patent number
US07579351B2

Reaction notes

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