Hydrochloric Acid → 1,3,4,5-Tetrahydro-3-[1-(phenylmethyl)-4-piperidinyl]-2H-1,3-benzodiazepin-2-one

HRID 1452711Notes

Reaction equation

C[O:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][C:13]([NH:15][CH:16]1[CH2:21][CH2:20][N:19]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:18][CH2:17]1)=O)=O.[H-].C([Al+]CC(C)C)C(C)C.Cl.[OH-].[Na+]>C1(C)C=CC=CC=1>[C:23]1([CH2:22][N:19]2[CH2:18][CH2:17][CH:16]([N:15]3[CH2:13][CH2:12][C:7]4[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=4[NH:5][C:3]3=[O:2])[CH2:21][CH2:20]2)[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

Conditions

Temperature: 80 °C

Procedure

5.00 g (13.11 mmol, 1.0 eq) 2-methoxycarbonylamino-N-[1-(phenylmethyl)-4-piperidinyl]-phenylacetamide from Example 3 are suspended in 50 ml of toluene and heated to 80° C. At this temperature 56.1 g (78.61 mmol, 6.0 eq) diisobutylaluminium hydride in toluene (20%) are metered in. After the addition has ended the reaction mixture is stirred for another 30 minutes at this temperature. After cooling to 10° C. the mixture is adjusted to pH=2.5 with hydrochloric acid. The precipitate formed is dissolved with sodium hydroxide solution and after phase separation the organic phase is washed with 50 ml of water. The organic phase is evaporated down in vacuo to an oil and combined with 50 ml of methanol.

Workup

additionAfter the addition
temperatureAfter cooling to 10° C. the mixture
customThe precipitate formed
customafter phase separation the organic phase
washis washed with 50 ml of water
customThe organic phase is evaporated down in vacuo to an oil

Sources & evidence

ORD record: ord-c8423b4bfba7440093ea8d11f0db2509
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07473778B2

Reaction notes

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