Potassium Bromide → 1-[3-(Trifluoromethyl)phenyl]-1,4-diazepane

HRID 1250160Notes

Reaction equation

C(OC([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[K+].[Br-]>>[F:24][C:21]([F:22])([F:23])[C:17]1[CH:16]=[C:15]([N:11]2[CH2:12][CH2:13][CH2:14][NH:8][CH2:9][CH2:10]2)[CH:20]=[CH:19][CH:18]=1

Participants

Reactant 2

HCID 253877Potassium Bromide

HCID 69365142HCID 69365142, compound

Product 1

HCID 151247971-[3-(Trifluoromethyl)phenyl]-1,4-diazepaneYield 91%

Procedure

The title compound was prepared according to the procedure of Example 1, Step 6 except that 4-(3-trifluoromethyl-phenyl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester was used in place of 4-(2-methoxy-phenyl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester. Yield: 91%; 1H NMR (300 MHz, CDCl3): δ1.77 (brs, 1H), 1.92 (pent, J=5.9 Hz, 2H), 2.84 (t, J=5.8 Hz, 2H), 3.04 (t, J=5.4 Hz, 2H), 3.56-3.62 (m, 4H), 6.77-6.88 (m, 3H), 7.29 (d, J=7.7 Hz, 1H); IR (KBr, cm−1): 3286w; MS (ES) m/z (relative intensity): 245 (M++H, 60). Anal. Calcd. for C12H15F3N2: C, 59.01; H, 6.19; N, 11.47. Found: C, 58.56; H, 6.03; N, 10.98.

Sources & evidence

ORD record: ord-c780bded4edd40f9811720c63fa22a65
Source dataset: uspto-grants-2002_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06337326B1

Reaction notes

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